Oxa-and thia(di)azabicyclic compounds

ABSTRACT

PCT No. PCT/US94/09522 Sec. 371 Date Feb. 28, 1996 Sec. 102(e) Date Feb. 28, 1996 PCT Filed Aug. 30, 1994 PCT Pub. No. WO95/06643 PCT Pub. Date Mar. 9, 1995The present invention relates to oxa(di)azabicyclic and thia(di)azabicyclic compounds, a method for their preparation and their use as herbicides.

The present invention relates to novel oxa(di)azabicyclic and thia(di)azabicyclic compounds, a method for their preparation and their use as weedkillers.

As has already been reported, certain thiadiazabicyclic compounds (see EP 238 711, EP 304 920, U.S. Pat. Nos. 4,885,023, 4,684,397, US 4,801,408, WO 92/21684 and EP 600 833) can be used as weedkillers.

The present invention provides novel compounds of Formula I, ##STR1## wherein: X is selected from the group O, S, S(O), S(O)₂, CH₂, CHF, CF₂, CHCl, CHBr, CHOCH₂ F, CHOCHF₂, CHOCF₃, CHOCH₂ CF₃ and NR⁴ ;

m and n are independently 1 or 2, where m+n=2 or 3;

p is 0 to 9;

U is N or CH;

W is independently O or S;

R^(A) is independently selected from the group halogen, C₁ -C₄ alkyl, cyano, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₂ -C₄ alkylcarbonyl, OR³, C₂ -C₆ alkyloxycarbonyl, C₂ -C₆ haloalkoxycarbonyl, and C₃ -C₈ alkoxycarbonylalkyl; or, two R^(A) groups on the same carbon atom, together with this carbon, are C═O;

R³ is selected from the group hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkylcarbonyl and C₂ -C₄ haloalkylcarbonyl;

R⁴ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₂ -C₄ alkylcarbonyl, C₂ -C₄ haloalkoxycarbonyl and C₂ -C₄ alkoxycarbonyl;

provided that:

i) when X is CH₂ and U is N, then p is 1 to 8 and at least one R^(A) is halogen; and

ii) when X is CHOCH₂ F, CHOCHF₂, CHOCF₃, or CHOCH₂ CF₃, m and n are 1, and U is N, then p is 1 to 5 and at least one R^(A) is other than alkyl;

Q is selected from the group ##STR2## Z is O or S; R⁵ is hydrogen or halogen;

R⁶ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, OCH₃, SCH₃, OCHF₂, halogen, CN and NO₂ ;

R⁷ is selected from the group hydrogen, C₁ -C₈ alkyl, C₁ -C₈ haloalkyl, halogen, OR¹¹, SR¹¹, S(O)_(q) R¹¹, COR¹¹, CO₂ R¹¹, C(O)SR¹¹, C(O)NR¹² R¹³, CHO and NHSO₂ NHR¹⁶ ;

R⁸ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and halogen;

R⁹ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and halogen; or, when Q is Q-2 or Q-6, R⁸ and R⁹ together with the carbon to which they are bonded is additionally selected from C═O;

R¹⁰ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkoxyalkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkenyl;

R¹¹ is selected from the group C₁ -C₈ alkyl, C₃ -C₈ cycloalkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkenyl, C₁ -C₈ haloalkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, C₂ -C₈ alkylsulphinylalkyl, C₂ -C₈ alkylsulphonylalkyl, C₃ -C₈ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl, C₂ -C₄ carboxyalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₆ -C₈ alkenyloxycarbonylalkyl, C₆ -C₈ alkenyloxycarbonylalkyl, C₅ -C₈ alkoxycarbonylalkenyl, C₄ -C₈ alkenyloxyalkyl, C₆ -C₈ cycloalkoxyalkyl, C₄ -C₈ alkynyloxyalkyl, C₃ -C₈ haloalkoxyalkyl, C₄ -C₈ haloalkenyloxyalkyl, C₄ -C₈ haloalkynyloxyalkyl, C₄ -C₈ alkenylthioalkyl, C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted with phenoxy or benzyloxy, each of the phenoxy and benzyloxy optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl, C₄ -C₈ trialkylsilylalkyl, C₃ -C₈ cyanoalkyl, C₃ -C₈ halocycloalkyl, C₃ -C₈ haloalkenyl, C₅ -C₈ alkoxyalkenyl, C₅ -C₈ haloalkoxyalkenyl, C₅ -C₈ alkylthioalkenyl, C₃ -C₈ haloalkynyl, C₅ -C₈ alkoxyalkynyl, C₅ -C₈ haloalkoxyalkynyl, C₅ -C₈ alkylthioalkynyl, C₂ -C₈ alkylcarbonyl; benzyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁷ COR¹⁸, CHR⁷ P(O)(ORI¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S)(OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O)NH₂, phenyl and pyridyl, each of the phenyl and pyridyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy and CHR¹⁷ CH═NOR¹⁸ ;

R¹² and R¹⁴ are independently hydrogen or C₁ -C₄ alkyl;

R¹³ and R¹⁵ are independently selected from the group C₁ -C₄ alkyl and phenyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and C₁ -C₄ alkoxy; or

R¹² and R¹³ are taken together as --(CH₂)₅ --, --(CH₂)₄ -- or --CH₂ CH₂ OCH₂ CH₂ --, each independently forming a ring in which one or more H atoms is optionally replaced by at least one member independently selected from the group C₁ -C₃ alkyl, optionally substituted phenyl and optionally substituted benzyl; or

R¹⁴ and R¹⁵ together with the carbon atom to which they are attached is C₃ -C₈ cycloalkyl;

R¹⁶ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl;

R¹⁷ is hydrogen or C₁ -C₃ alkyl;

R¹⁸ is selected from the group C₁ -C₆ alkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkynyl; and

q is 1 or2.

In the definitions given above the term `alkyl`, alone or in combined names such as `alkylthio` or `haloalkyl`, includes a straight or branched chain isomers; for example, methyl, ethyl, n-propyl, isopropyl or the various butyl isomers. Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyl oxy and the various butyl oxy isomers. Alkenyl covers straight- or branch-chain alkenes; for example, 1-propenyl, 2-propenyl, 3-propenyl and the various butenyl isomers. Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term `halogen`, alone or in combined names such as `haloalkyl`, signifies fluorine, chlorine, bromine or iodine. Furthermore, if `haloalkyl` is used in the combined name, alkyl can be partly or totally substituted with halogen atoms, which in turn can be identical or different. Examples of haloalkyl are CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFC₁. Brackets in the nomenclature signify an optional component; for example, thia(di)azabicyclic compounds represent the aza- or the dim-compound.

Preference is given to the following radicals,

wherein:

X is selected from the group O, CHF, CF₂ and CHCl;

R^(A) is independently selected from the group fluorine, chlorine and bromine;

R⁵ is selected from the group hydrogen, fluorine and chlorine;

R⁶ is selected from the group chlorine, bromine and cyano;

R⁷ is selected from the group hydrogen, OR¹¹, CO₂ R¹¹, C₁ -C₂ alkyl and C₁ -C₂ haloalkyl;

R¹⁰ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, C₃ -C₄ alkenyl and C₃ -C₄ alkynyl;

R¹¹ is selected from the group C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkylthioalkyl, C₂ -C₄ alkylsulphinylalkyl, C₂ -C₄ alkylsulphonylalkyl, C₃ -C₆ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl, C₂ -C₄ carboxyalkyl, C₃ -C₆ alkoxycarbonylalkyl, C₆ -C₈ alkenyloxycarbonylalkyl, C₆ -C₈ alkynyloxycarbonylalkyl, C₅ -C₆ alkoxycarbonylalkenyl, C₆ -C₈ cycloalkoxyalkyl, C₄ -C₆ alkenyloxyalkyl, C₄ -C₆ alkynyloxyalkyl, C₃ -C₆ haloalkoxyalkyl, C₄ -C₈ haloalkenoxyalkyl, C₄ -C₆ haloalkynyloxyalkyl, C₆ -C₈ cycloalkylthioalkyl, C₄ -C₆ alkenylthioalkyl, C₄ -C₆ alkynylthioalkyl; C₁ -C₂ alkyl substituted with phenoxy or benzyloxy, each of the phenoxy and benzyloxy optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; C₄ -C₈ trialkylsilylalkyl, C₃ -C₄ cyanoalkyl, C₃ -C₆ halocycloalkyl, C₃ -C₆ haloalkenyl, C₅ -C₆ alkoxyalkenyl, C₅ -C₆ haloalkoxyalkenyl, C₅ -C₆ alkylthioalkenyl, C₃ -C₆ haloalkynyl, C₅ -C₆ alkoxyalkynyl, C₅ -C₆ haloalkoxyalkynyl, C₅ -C₆ alkylthioalkynyl, C₂ -C₄ alkylcarbonyl, benzyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₂ alkyl and C₁ -C₂ haloalkyl; CHR¹⁷ COR¹⁸, CHR¹⁷ P(O)(OR¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S)(OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O)NH₂, phenyl and pyridyl, each of the phenyl and pyridyl optionally substituted with at least one member independently selected from the group fluorine, chlorine, bromine, C₁ -C₂ alkylhaloalkyl and C₁ 1∝C₂ alkoxy;

R¹² is hydrogen or C₁ -C₂ alkyl;

R¹³ is selected from the group C₁ -C₂ alkyl and phenyl optionally substituted with at least one member selected from the group fluorine, chlorine, bromine, C₁ -C₂ alkyl, C₁ -C₂ haloalkyl and C₁ -C₂ alkoxy; or

R¹² and R¹³ are taken together as --(CH₂)₅ --, --(CH₂)₄ -- or --CH₂ CH₂ OCH₂ CH₂ --, each independently forming a ring in which one or more H atoms is optionally and independently replaced by C₁ -C₂ alkyl;

R¹⁷ is hydrogen or C₁ -C₂ alkyl; and

R¹⁸ is selected from the group C₁ -C₂ alkyl, C₃ -C₄ alkenyl and C₃ -C₄ alkynyl.

Compounds of Formula I can exist as one or more stereoisomers. The various stereoisomers comprise enantiomers, diastereomers and geometric isomers. The skilled person knows that a stereoisomer may be more active and how the cited enantiomers, diastereomers and geometric isomers can be separated. Accordingly, the present invention covers racemic mixtures, individual stereoisomers and optically active mixtures of compounds of Formula I.

The novel oxa- or thiaazabicyclic compounds of general Formula Ia, ##STR3## wherein n, m, p, X, W, R^(A) and Q have the meanings given above, are obtained according to the present invention by reacting an aryliso(thio)cyanate of Formula II,

    Q-NCW                                                      II

wherein W and Q have the meanings given above, with a (thio)carboxylic acid or ester of Formula III, ##STR4## wherein n, m, p, X, W, and R^(A) have the meanings given above and R represents hydroxy, C₁ -C₄ alkoxy, halogen or O-active esters, for example O-succinimide esters or anhydrides (see Houben-Weyl, Vol. 25/1 and 25/2 (1974)) optionally in the presence of an acid acceptor and a diluent.

The invention also provides a method for preparation of compounds of Formula I by reacting a compound of Formula IV, ##STR5## wherein n, m, p, X, R^(A), R⁵ and R⁶ have the meanings given above and Y=O, S, or NH, with an electrophile of Formula V, VI or VII, ##STR6## wherein Z is a chlorine, bromine or iodine atom or O--SO₂ CH₃, O--SO₂ CF₃, O--SO₂ --Ph, O--SO₂ -(4-methylphenyl) and R¹¹ and R¹⁶ have the meanings given above.

The invention a/so provides a method for preparation of compounds of Formula I, wherein m, n, p, X, R^(A), W and Q have the meanings given above, comprising reacting a compound of Formula HI, wherein R is hydroxy, (C₁ -C₄) alkoxy, halogen or O-active ester, with thiophosgene or with a thiophosgene-substitute XV, wherein L₁ and L₂ are independently appropriate leaving groups, to produce compounds of Formula VIII, which are then reacted with compounds of Formula IX to form compounds of Formula X, ##STR7## and, finally, convening the compounds of Formula X to compounds of Formula I by cyclization.

The invention also provides a method for preparation of compounds of Formula Ib ##STR8## wherein n, W and Q have the meanings given above and R¹, R¹⁹ and X have the meanings given below, by reacting a compound of Formula XI, ##STR9## wherein X is O, S, or NR⁴, R¹ is independently R^(A) or hydrogen, and R¹⁹ is independently selected from the group hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or C₃ -C₄ alkenyl, with a compound of Formula XVb,

    CWCl.sub.2                                                 XVb

wherein W has the meaning given above, preferably in an inert organic solvent, for example in an aromatic solvent such as toluene or chlorobenzene, in a halogensted hydrocarbon such as chloroform or methylene chloride, in an ether such as diisopropylether or in acetonitrile or dimethylformamide, preferably by means of base catalysis and preferably at temperatures of 0°-120° C. Bases or organic bases, for example organic amines such as triethylamine, are preferably used, but pyridine may also be used, preferably in the presence of activate_(d) charcoal.

Compounds of Formula XI can be obtained by reacting compounds of Formula XIII, ##STR10## wherein X is 0, S, or NR⁴, and n, R¹, R⁴, W and Q have the meanings given above, with ketones or aldehydes of Formula XII ##STR11## or with phosgene or a phosgene substitute. In Formula XII, R¹⁹ has the meaning given above. C═O is obtained in the ring upon reaction with phosgene or phosgene substitute. The reaction is preferably carried out in an inert organic solvent, for example in an aromatic solvent such as toluene or chlorobenzene, a halogenated hydrocarbon such as chloroform or methylene chloride, an ether such as diisopropylether or in acetonitrile or dimethylformamide, preferably by means of acid catalysis and preferably at temperatures of 20°-120° C. Preferred acids are organic acids, for example organic sulfonic acids such as p-toluenesulfonic acid.

Compounds of Formula XII are obtained by reacting 2-mercapto-, 2-hydroxyalkylhydrazines or 2-aminoalkylhydrazines of Formula XIV, ##STR12## wherein X is O, S, or NR⁴ and R¹ and R⁴ have the meanings given above, with aryliso(thio)cyanates of Formula II, wherein Q has the meaning given above, preferably in an inert organic solvent, for example in an aromatic solvent such as toluene or chlorobenzene, in a halogensted hydrocarbon such as chloroform or methylene chloride, in an ether such as diisopropylether or in acetonitrile or dimethylformamide or alcohols, such as methanol or ethanol, preferably by means of base catalysis and preferably at temperatures of 20°-120° C. Bases or organic bases, for example organic amines such as triethylamine, but also pyridine, are preferably used.

In the reaction of a compound of Formula II with a compound of Formula III when R=alkyl, the reaction is carried out in an inert organic solvent, for example in an aromatic solvent such as toluene or chlorobenzene, in a halogenated hydrocarbon such as chloroform or methylene chloride, in an ether such as diisopropylether or tetrahydrofuran or in acetonitrile or dimethylformamide, optionally with base catalysis at temperatures between -20° C. and 125° C. Organic bases, for example organic amines such as triethylamine or even pyridine or also for example inorganic bases such as potassium carbonate (see EP-A10 272 594) are preferably used as bases. Variants of the general method A are described in EP-A2 0 070 389.

In the case where R=hydroxy, the reaction is carded out in water or methanol as solvent or, preferably, in a biphasic water/organic solvent system. Particular preference is given to the method in which a compound of Formula III, optionally salts of III, is added in water together with an inorganic base, for example an alkali- or alkaline earth metal hydroxide, carbonate or bicarbonate such as sodium hydrolide or potassium carbonate, or together with an organic base, for example, an organic amine such as triethylamine, followed by addition of compounds of Formula II dissolved in an inert solvent, for example, toluene, chlorobenzene or chloroform. Compounds II can, if necessary, also be added directly to the aqueous or alcoholic solution. The reaction mixture is then kept for several days, preferably for between 3 and 50 hours, at temperatures of between -40° C. and +50° C., preferably between -10° C. and +30° C.

The aqueous phase is then adjusted to a pH between 1 and 3 with acid, preferably an inorganic acid such as aqueous hydrochloric or sulphuric acid. The thiourea derivatives (see compounds X) thus produced are then cyclized at temperatures of between 0° C. and 100° C., optionally in the presence of an acid such as hydrochloric acid and/or formic acid, or with the aid of a dehydrating substance, for example, dicyclohexylcarbodiimide (DCC), in a solvent known to the skilled person (for example, acetonitrile), or optionally by conversion into an ester (R=alkyl or active ester) by known methods (see Houben-Weyl, Methoden der organischen Chemie, Vol. XV (1974)).

The compounds of Formula II are known or can be prepared by known methods; for these see EP 304 920, EP 238 711, EP 409 025, EP 373 461, EP 311 135 and DE 37 24 096.

Amines of Formula III are known and can be prepared by the known methods; for these see for example M. Sekiya et al., Chem. Pharm. Bull. (1983), 31(1), p 94; J. M. Cassal, A. Furst, W. Meier. Helv. Chim. Acta (1976), 59(6), p 1917; S. -K. Tsui, J. D. Wood, Can. J. Chem. (1979), 57(15), p 1977; M. Sekiya et al., Chem. Lett. (1982), (2), p 231.

EXAMPLE 1 N-Amino-N-(2-hydroxyethyl)-N'-(2 4-dichlorophenyl)thiourea

7.61 g (0.10 mol) 2-hydroxyethylhydrazine was dissolved in 100 mL methylene chloride at 0°-5° C. After dropwise addition of 10.2 g (0.10 tool) triethylamine, 20.4 g (0.10 mol) 2,4-dichlorophenylisothiocyanate dissolved in 70 mL methylene chloride was added over a period of 4 h. The reaction mixture was left to warm up to room temperature, stirred for a further 2 h, the precipitate filtered off, washed with methylene chloride and the desired compound isolated.

EXAMPLE 2 N-(2,4-Dichlorophenyl)tetrahydro-4H-1,3,4-oxadiazine-4-carbothioamide ##STR13##

1.72 g (6.20 mmol) N-amino-N-(2-hydroxyethyl)-N'-(2,4-dichlorophenyl)thiourea was suspended in 40 mL methylene chloride. 0.52 g (37% aqueous, 6.4 mmol) formaldehyde and a small quantity of p-toluenesulfonic acid were added before the reaction mixture was heated for 17 h in a Dean-Stark apparatus. The solvent was then removed and the desired product isolated.

EXAMPLE 3 1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H- 1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one ##STR14##

1.8 g (6.2 mmol) N-(2,4-dichlorophenyl)tetrahydro-4H-1,3,4-oxadiazine-4-carbothioamide was dissolved in 30 mL toluene and 1 mL triethylamine in the presence of a small quantity of activated charcoal at 0°-5° C. 3.49 g (6.81 mmol) phosgene as 20% solution in 30 mL toluene was added dropwise over 1.5 h. The reaction mixture was then left to warm up to room temperature and stirred overnight. The activated charcoal was removed by filtration and the solvent evaporated in vacuo. The desired product was isolated after chromatography on silica gel.

EXAMPLE 4 3- 4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl!imino!-6-fluorotetrahydro-1H,3H-pyrrolo 1,2-c!thiazol-1-one ##STR15##

A mixture of 1.31 g (0.01 mol) 4-fluoroproline, 30 mL 2N KOH in methanol and 10 mL water is prepared before 2.46 g (0.01 mol) 4-chloro-2-fluoro-5-isopropoxy-phenylisothiocyanate dissolved in 250 mL methanol is added dropwise. The reaction mixture is stirred overnight at room temperature, the aqueous phase adjusted to pH 2 and the resultant product (3.77 g, See Formula X) is filtered. The compound thus obtained is dissolved in 50 mL acetonitrile before 2.59 g (0.01 mol) dicyclohexylcarbodiimide is added at room temperature. The reaction mixture is stirred for 3 h and the crude product is purified by silica gel chromatography to give 3.24 g (85% yield) of the desired product.

EXAMPLE 5 3- 4-Chloro-2-fluoro-5-(propynyloxy)phenyl!imino!-6-fluorotetrahydro-1H,3H-pyrrolo 1,2c!thiazol-1-one ##STR16##

A mixture of 3.18 g (0.01 tool) 3- 4-chloro-2-fluoro-5-(1 -methylethoxy)phenyl!-imino!-6-fluorotetrahydro-1H,3H-pyrrolo l,2-c!thiazol-l-one, 6.95 g (0.05 tool) potassium carbonate, 1.78 g (12.0 mmol) propargyl bromide and 60 mL acetonitrile is stirred for 20 h at room temperature. The reaction mixture is adjusted to pH 2 with 5% aqueous hydrochloric acid and extracted with diethylether (3×15 mL). The organic phase is then dried, the solvent distilled off in vacuo and the crude product purified on a silica gel column.

                  TABLE 1                                                          ______________________________________                                          ##STR17##                                                                     R.sup.1                                                                            R.sup.1                                                                              R.sup.5                                                                              R.sup.6                                                                            R.sup.7           X                                        ______________________________________                                         H   H     F     Cl  H                 O                                        H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      O                                        H   H     F     Cl  CO.sub.2 CH.sub.3 O                                        H   H     F     Cl  CO.sub.2 C.sub.2 H.sub.5                                                                         O                                        H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CF.sub.3                                                                    O                                        H   H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                              O                                        H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           O                                        H   H     F     Cl  CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                             O                                        H   H     F     Cl  CO.sub.2 CH.sub.2 CCH                                                                            O                                        H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CCH                                                                         O                                        H   H     F     Cl  CO.sub.2 CH.sub.2 CF.sub.3                                                                       O                                        H   H     F     Cl  CON(CH.sub.3).sub.2                                                                              O                                        H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5                                                    O                                        H   H     F     Cl  OCH.sub.3         O                                        H   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              O                                        H   H     F     Cl  OCH.sub.2 CCH     O                                        H   H     F     Cl  OCH(CH.sub.3)CCH  O                                        H   H     F     Cl  OCH.sub.2 C(O)N(CH.sub.3).sub.2                                                                  O                                        H   H     F     Cl  OCH.sub.2 P(O)(OC.sub.2 H.sub.5).sub.2                                                           O                                        H   H     F     Cl  OCH.sub.2 P(S)(OC.sub.2 H.sub.5).sub.2                                                           O                                        H   H     F     Cl  OCF.sub.2 CHFCl   O                                        H   H     F     Cl  OCHF.sub.2        O                                        H   H     F     Cl  OCH.sub.2 CHCH.sub.2                                                                             O                                        H   H     F     Cl  OCH.sub.2 CHCHCl  O                                        H   H     F     Cl  OCH.sub.2 C(Cl)CH.sub.2                                                                          O                                        H   H     F     Cl  SCH.sub.2 CO.sub.2 H                                                                             O                                        H   H     F     Cl  SCH.sub.2 CO.sub.2 CH.sub.3                                                                      O                                        H   H     F     Cl  NHSO.sub.2 CH.sub.3                                                                              O                                        H   H     F     Cl  NHSO.sub.2 CF.sub.3                                                                              O                                        H   H     F     Cl  NHSO.sub.2 CH(CH.sub.3).sub.2                                                                    O                                        H   H     F     Cl  NHSO.sub.2 NHCH.sub.3                                                                            O                                        H   H     H     Cl  H                 CHF                                      H   H     F     Cl  H                 CHF                                      H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.3 CHF                                      H   H     F     Cl  CO.sub.2 C.sub.2 H.sub.5                                                                         CHF                                      H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CF.sub.3                                                                    CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                              CHF                                      H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                             CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.2 CCH                                                                            CHF                                      H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CCH                                                                         CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.2 CF.sub.3                                                                       CHF                                      H   H     F     Cl  CON(CH.sub.3).sub.2                                                                              CHF                                      H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5                                                    CHF                                      H   H     F     Cl  OCH.sub.3         CHF                                      H   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              CHF                                      H   H     F     Cl  OCH.sub.2 CCH     CHF                                      H   H     F     Cl  OCH(CH.sub.3)CCH  CHF                                      H   H     F     Cl  OCH.sub.2 C(O)N(CH.sub.3).sub.2                                                                  CHF                                      H   H     F     Cl  OCH.sub.2 P(O)(OC.sub.2 H.sub.5).sub.2                                                           CHF                                      H   H     F     Cl  OCH.sub.2 P(S)(OC.sub.2 H.sub.5).sub.2                                                           CHF                                      H   H     F     Cl  OCF.sub.2 CHFCl   CHF                                      H   H     F     Cl  OCHF.sub.2        CHF                                      H   H     F     Cl  OCH.sub.2 CHCH.sub.2                                                                             CHF                                      H   H     F     Cl  OCH.sub.2 CHCHCl  CHF                                      H   H     F     Cl  OCH.sub.2 C(Cl)CH.sub.2                                                                          CHF                                      H   H     F     Cl  CN                CHF                                      H   H     F     Cl  SCH.sub.2 CO.sub.2 H                                                                             CHF                                      H   H     F     Cl  SCH(CH.sub.3).sub.2                                                                              CHF                                      H   H     F     Cl  SCH.sub.2 CO.sub.2 CH.sub.3                                                                      CHF                                      H   H     F     Cl  SCH.sub.2 CCH     CHF                                      H   H     F     Cl  NHSO.sub.2 CH.sub.3                                                                              CHF                                      H   H     F     Cl  NHSO.sub.2 CF.sub.3                                                                              CHF                                      H   H     F     Cl  NHSO.sub.2 CH(CH.sub.3).sub.2                                                                    CHF                                      H   H     F     Cl  NHSO.sub.2 NHCH.sub.3                                                                            CHF                                      H   H     F     Cl  OCH.sub.2 CO.sub.2 C.sub.5 H.sub.11                                                              CHF                                      H   H     F     Cl  OCH.sub.2 CHNOCH.sub.3                                                                           CHF                                      H   H     F     Cl  OCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                                                CHF                                      H   H     F     Cl  OCH.sub.2 Si(CH.sub.3).sub.3                                                                     CHF                                      H   H     F     Cl                                                                                  ##STR18##        CHF                                      H   H     Cl    Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHF                                      H   H     Cl    Cl  OCH.sub.2 CCH     CHF                                      H   H     Cl    Cl  CO.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                             CHF                                      H   H     Cl    CN  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHF                                      H   H     Cl    CN  CO.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                             CHF                                      F   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CH.sub.2                                 F   H     F     Cl  CO.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                             CH.sub.2                                 F   H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.2 CCl.sub.3                                                             CH.sub.2                                 F   H     F     Cl  OCH.sub.2 CCH     CH.sub.2                                 F   H     F     Cl  OCH(CH.sub.3)CCH  CH.sub.2                                 F   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              CH.sub.2                                 F   H     F     Cl  CO.sub.2 CH.sub.3 CH.sub.2                                 F   H     F     Cl  SCH.sub.2 CO.sub.2 H                                                                             CH.sub.2                                 H   H     Cl    Cl  H                 CH.sub.2                                 H   H     Cl    Cl  H                 CH.sub.2                                 H   H     Cl    Cl  Cl                CH.sub.2                                 F   H     F     Cl  CO.sub.2 C.sub.2 H.sub.5                                                                         CH.sub.2                                 F   H     F     Cl  SCH.sub.2 CO.sub.2 Me                                                                            CH.sub.2                                 F   H     F     Cl  NHSO.sub.2 CH.sub.3                                                                              CH.sub.2                                 F   H     F     Cl  NHSO.sub.2 C.sub.2 H.sub.5                                                                       CH.sub.2                                 H   H     F     Cl  CO.sub.2 CH.sub.3 CHCl                                     H   H     F     Cl  CO.sub.2 C.sub.2 H.sub.5                                                                         CHCl                                     H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHCl                                     H   H     F     Cl  CO.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                             CHCl                                     H   H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                              CHCl                                     H   H     F     Cl  CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                             CHCl                                     H   H     F     Cl  SCH.sub.2 CO.sub.2 Me                                                                            CHCl                                     H   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              CHCl                                     H   H     F     Cl  SCH.sub.2 CO.sub.2 H                                                                             CHCl                                     H   H     F     Cl  OCH.sub.2 CCH     CHCl                                     H   H     F     Cl  OCH(CH.sub.3)CCH  CHCl                                     H   H     F     Cl  NHSO.sub.2 CH.sub.3                                                                              CHCl                                     H   H     F     Cl  NHSO.sub.2 C.sub.2 H.sub.5                                                                       CHCl                                     H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHBr                                     H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           CHBr                                     H   H     F     Cl  OCH.sub.3         CHBr                                     H   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              CHBr                                     H   H     F     Cl  OCH.sub.2 CCH     CHBr                                     H   H     F     Cl  OCH(CH.sub.3)CCH  CHBr                                     H   H     F     Cl  OCH.sub.2 CHCH.sub.2                                                                             CHBr                                     H   H     F     Cl  SCH.sub.2 CO.sub.2 Me                                                                            CHBr                                     H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHOCHF.sub.2                             H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           CHOCHF.sub.2                             H   H     F     Cl  OCH.sub.3         CHOCHF.sub.2                             H   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              CHOCHF.sub.2                             H   H     F     Cl  OCH.sub.2 CCH     CHOCHF.sub.2                             H   H     F     Cl  OCH(CH.sub.3)CCH CHOCHF.sub.2                              H   H     F     Cl  OCH.sub.2 CHCH.sub.2                                                                             CHOCHF.sub.2                             H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHOCF.sub.3                              H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           CHOCF.sub.3                              H   H     F     Cl  OCH.sub.3         CHOCF.sub.3                              H   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              CHOCF.sub.3                              H   H     F     Cl  OCH.sub.2 CCH     CHOCF.sub.3                              H   H     F     Cl  OCH(CH.sub.3)CCH  CHOCF.sub.3                              H   H     F     Cl  OCH.sub.2 CHCH.sub.2                                                                             CHOCF.sub.3                              H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                      CHOCH.sub.2 CF.sub.3                     H   H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           CHOCH.sub.2 CF.sub.3                     H   H     F     Cl  OCH.sub.3         CHOCH.sub.2 CF.sub.3                     H   H     F     Cl  OCH(CH.sub.3).sub.2                                                                              CHOCH.sub.2 CF.sub.3                     H   H     F     Cl  OCH.sub.2 CCH     CHOCH.sub.2 CF.sub.3                     H   H     F     Cl  OCH(CH.sub.3 (CCH CHOCH.sub.2 CF.sub.3                     H   H     F     Cl  OCH.sub.2 CHCH.sub.2                                                                             CHOCH.sub.2 CF.sub.3                     ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR19##                                                                     R.sup.1                                                                            R.sup.1                                                                               R.sup.5                                                                              R.sup.6                                                                               R.sup.8                                                                             R.sup.9 X        W                                ______________________________________                                         H   H      F     Cl     H    CH.sub.3                                                                               O        O                                H   H      F     Cl     H    CH.sub.3                                                                               CHF      O                                H   H      F     Cl     CH.sub.3                                                                            CH.sub.3                                                                               CHF      O                                H   H      F     Cl     H    CH.sub.2 F                                                                             CHF      O                                H   H      F     Cl     H    CH.sub.2 Cl                                                                            CHF      O                                H   H      F     Cl     H    CH.sub.2 Br                                                                            CHF      O                                H   H      F     Cl     H    CH(CH.sub.3).sub.2                                                                     CHF      O                                H   H      F     Cl     H    CH.sub.2 CH.sub.3                                                                      CHF      O                                H   H      F     Br     H    CH.sub.3                                                                               CHF      O                                H   H      F     OCH.sub.3                                                                             H    CH.sub.3                                                                               CHF      O                                H   H      F     CH.sub.3                                                                              H    CH.sub.3                                                                               CHF      O                                H   H      F     CN     H    CH.sub.3                                                                               CHF      O                                H   H      F     CF.sub.3                                                                              H    CH.sub.3                                                                               CHF      O                                H   H      F     OCHF.sub.2                                                                            H    CH.sub.3                                                                               CHF      O                                H   H      F     Cl     H    CH.sub.3                                                                               CHF      S                                H   H      F     Cl     H    CH.sub.3                                                                               O        S                                F   H      F     Cl     H    CH.sub.3                                                                               CH.sub.2 O                                H   H      F     Cl     H    CH.sub.3                                                                               CHCl     O                                F   H      F     Cl     H    CH.sub.3                                                                               CH.sub.2 S                                H   H      F     Cl     H    CH.sub.3                                                                               CHCl     S                                H   H      F     Cl     H    CH.sub.3                                                                               CHBr     O                                H   H      F     Cl     H    CH.sub.3                                                                               CHOCHF.sub.2                                                                            O                                H   H      F     Cl     H    CH.sub.3                                                                               CHOCF.sub.3                                                                             O                                H   H      F     Cl     H    CH.sub.3                                                                               CHOCH.sub.2 CF.sub.3                                                                    O                                ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR20##                                                                     R.sup.1                                                                            R.sup.1                                                                               R.sup.5                                                                               R.sup.6                                                                              R.sup.8                                                                              R.sup.9                                                                              X         W                                ______________________________________                                         H   H      F      Cl    H     Cl    O         S                                H   H      F      Cl    H     CH.sub.3                                                                             O         S                                H   H      F      Cl    H     H     CHF       S                                H   H      F      Cl    H     Cl    CHF       S                                H   H      F      Cl    H     CH.sub.3                                                                             CHF       S                                H   H      F      Cl    CH.sub.3                                                                             CH.sub.3                                                                             CHF       S                                H   H      H      SCH.sub.3                                                                            H     H     CHF       S                                H   H      F      Cl    H     Cl    CHCl      S                                F   H      F      Cl    H     Cl    CH.sub.2  S                                H   H      F      Cl    H     CH.sub.3                                                                             CHCl      S                                F   H      F      Cl    H     CH.sub.3                                                                             CH.sub.2  S                                H   H      F      Cl    H     Cl    CHF       O                                H   H      F      Cl    H     H     CHF       O                                H   H      F      Cl    H     CH.sub.3                                                                             CHF       O                                H   H      F      Cl    H     C.sub.2 H.sub.5                                                                      CHF       S                                H   H      F      Cl    H     Cl    CHBr      S                                H   H      F      Cl    H     CH.sub.3                                                                             CHBr      S                                H   H      F      Cl    H     Cl    CHOCHF.sub.2                                                                             S                                H   H      F      Cl    H     CH.sub.3                                                                             CHOCHF.sub.2                                                                             S                                H   H      F      Cl    H     Cl    CHOCF.sub.3                                                                              S                                H   H      F      Cl    H     CH.sub.3                                                                             CHOCF.sub.3                                                                              S                                H   H      F      Cl    H     Cl    CHOCH.sub.2 CF.sub.3                                                                     S                                ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR21##                                                                     R.sup.1                                                                             R.sup.1                                                                               R.sup.5                                                                               R.sup.10     X         W                                    ______________________________________                                         H    H      F      CH.sub.2 CCH O         S                                    H    H      F      CH.sub.2 CHCH.sub.2                                                                         O         S                                    H    H      F      H            CHF       S                                    H    H      F      CH.sub.3     CHF       S                                    H    H      F      CH.sub.2 CCH CHF       S                                    H    H      F      CH(CH.sub.3)CCH                                                                             CHF       S                                    H    H      F      CH.sub.2 CHCH.sub.2                                                                         CHF       S                                    H    H      F      CH.sub.2 OCH.sub.3                                                                          CHF       S                                    H    H      F      CH(CH.sub.3).sub.2                                                                          CHF       S                                    H    H      F      CHF.sub.2    CHF       S                                    H    H      F      CF.sub.2 CHF.sub.2                                                                          CHF       S                                    H    H      F      CH.sub.2 CHCHCH.sub.3                                                                       CHF       S                                    H    H      F      CH.sub.2 CH.sub.2 CH.sub.3                                                                  CHF       S                                    H    H      F      CH.sub.2 CCH CHF       O                                    H    H      F      CH.sub.2 CHCH.sub.2                                                                         CHF       O                                    H    H      Cl     CH.sub.2 CCH CHF       S                                    F    H      F      CH.sub.2 CCH CHF       S                                    F    H      F      CH.sub.2 CHCH.sub.2                                                                         CHF       S                                    H    H      F      CH.sub.2 CCH CHCl      S                                    H    H      F      CH.sub.2 CHCH.sub.2                                                                         CHCl      S                                    H    H      F      CH.sub.3     CHCl      S                                    H    H      F      CH.sub.2 CCH CHBr      S                                    H    H      F      CH.sub.2 CHCH.sub.2                                                                         CHBr      S                                    H    H      F      CH.sub.2 CCH CHBr      O                                    H    H      F      CH.sub.2 CCH CHOCHF.sub.2                                                                             S                                    H    H      F      CH.sub.2 CCH CHOCF.sub.3                                                                              S                                    H    H      F      CH.sub.2 CCH CHOCH.sub.2 CF.sub.3                                                                     S                                    ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR22##                                                                                      ##STR23##                                                     R.sup.1                                                                            R.sup.1                                                                              R.sup.5                                                                              R.sup.8                                                                            R.sup.9                                                                             R.sup.10   X         W                                ______________________________________                                         H   H     F     H   H    CH.sub.2 C CH                                                                             O         O                                H   H     F     H   H    CH.sub.2 CHCH.sub.2                                                                       O         O                                H   H     F     H   H    CH.sub.3   O         O                                H   H     H     H   H    CH.sub.3   CHF       O                                H   H     H     H   H    CH.sub.2 C CH                                                                             CHF       O                                H   H     F     H   H    CH.sub.3   CHF       O                                H   H     F     H   H    C.sub.2 H.sub.5                                                                           CHF       O                                H   H     F     H   H    CH(CH.sub.3).sub.2                                                                        CHF       O                                H   H     F     H   H    CH.sub.2 CH.sub.2 CH.sub.3                                                                CHF       O                                H   H     F     H   H    CH.sub.2 CHCH.sub.2                                                                       CHF       O                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHF       O                                H   H     F     H   H    CH(CH.sub.3)C CH                                                                          CHF       O                                H   H     H     H   H    CH.sub.2 C CH                                                                             CHF       S                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHF       S                                H   H     Cl    H   H    CH.sub.2 C CH                                                                             CHF       O                                H   H     F     H   CH.sub.3                                                                            CH.sub.2 C CH                                                                             CHF       O                                F   H     H     H   H    CH.sub.2 C CH                                                                             CH.sub.2  O                                F   H     F     H   H    CH.sub.3   CH.sub.2  O                                F   H     F     H   H    CH.sub.2 C CH                                                                             CH.sub.2  O                                F   H     F     H   H    CH.sub.2 CHCH.sub.2                                                                       CH.sub.2  O                                H   H     H     H   H    CH.sub.2 C CH                                                                             CHCl      O                                H   H     F     H   H    CH.sub.3   CHCl      O                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHCl      O                                H   H     F     H   H    CH.sub.2 CHCH.sub.2                                                                       CHCl      O                                H   H     F     H   H    CH.sub.2 CHCH.sub.2                                                                       CHCl      S                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHBr      O                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHBr      S                                H   H     F     H   H    CH.sub.2 CHCH.sub.2                                                                       CHBr      O                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHOCHF.sub.2                                                                             O                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHOCF.sub.3                                                                              O                                H   H     F     H   H    CH.sub.2 C CH                                                                             CHOCH.sub.2 CF.sub.3                                                                     O                                ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR24##                                                                                      ##STR25##                                                     R.sup.1 R.sup.1 R.sup.5 R.sup.8                                                                              R.sup.9                                                                              X                                          ______________________________________                                         H       H       H       F     F     O                                          H       H       F       F     F     O                                          H       H       F       H     H     O                                          H       H       H       F     F     CHF                                        H       H       F       F     F     CHF                                        H       H       F       H     H     CHF                                        F       H       H       F     F     CH.sub.2                                   F       H       F       F     F     CH.sub.2                                   F       H       F       H     H     CH.sub.2                                   H       H       H       F     F     CHCl                                       H       H       F       F     F     CHCl                                       H       H       F       H     H     CHCl                                       H       H       H       F     F     CHBr                                       H       H       F       F     F     CHBr                                       H       H       F       H     H     CHBr                                       H       H       F       F     F     CHOCHF.sub.2                               H       H       F       F     F     CHOCF.sub.3                                H       H       F       F     F     CHOCH.sub.2 CF.sub.3                       ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                          ##STR26##                                                                                      ##STR27##                                                     R.sup.1                                                                            R.sup.1                                                                              R.sup.5                                                                              R.sup.6                                                                            R.sup.7     R.sup.8                                                                              X                                        ______________________________________                                         H   H     H     H   CO.sub.2 CH.sub.3                                                                          H     O                                        H   H     H     H   CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             O                                        H   H     H     H   CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHF                                      H   H     H     H   CO.sub.2 C.sub.2 H.sub.5                                                                   CH.sub.3                                                                             CHF                                      H   H     H     H   CO.sub.2 C.sub.2 H.sub.5                                                                   H     CHF                                      H   H     H     H   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         CH.sub.3                                                                             CHF                                      H   H     H     H   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H     CHF                                      H   H     H     H   CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CHF                                      H   H     H     H   CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         H     CHF                                      H   H     H     H   CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CHF                                      H   H     H     Cl  CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHF                                      H   H     H     Cl  CO.sub.2 C.sub.2 H.sub.5                                                                   CH.sub.3                                                                             CHF                                      H   H     H     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         CH.sub.3                                                                             CHF                                      H   H     H     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CHF                                      H   H     H     Cl  CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHF                                      H   H     F     Cl  CO.sub.2 C.sub.2 H.sub.5                                                                   CH.sub.3                                                                             CHF                                      H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         CH.sub.3                                                                             CHF                                      H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H     CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.2 CH CH                                                                    CH.sub.3                                                                             CHF                                      H   H     F     Cl  CO.sub.2 CH(CH.sub.3)C CH                                                                  CH.sub.3                                                                             CHF                                      H   H     F     Cl  CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.3                                                                             CHF                                      F   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.3                                                                             CH.sub.2                                 F   H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CH.sub.2                                 F   H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     CH.sub.3                                                                             CH.sub.2                                 F   H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         CH.sub.3                                                                             CH.sub.2                                 F   H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CH.sub.2                                 H   H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.3                                                                             CHCl                                     H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         CH.sub.3                                                                             CHCl                                     H   H     F     Cl  CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHCl                                     H   H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                             CHCl                                     H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CHBr                                     H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         CH.sub.3                                                                             CHBr                                     H   H     F     Cl  CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHBr                                     H   H     F     Cl  CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHOCHF.sub.2                             H   H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                             CHOCHF.sub.2                             H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CHOCHF.sub.2                             H   H     F     Cl  CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHOCF.sub.3                              H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CHOCF.sub.3                              H   H     F     Cl  CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                             CHOCH.sub.2 CF.sub.3                     H   H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         CH.sub.3                                                                             CHOCH.sub.2 CF.sub.3                     F   H     H     H   CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CH.sub.2                                 F   H     H     Cl  CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CH.sub.2                                 F   H     F     Cl  CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CH.sub.2                                 F   H     F     Cl  CO.sub.2 CH(CH.sub.3)C CH                                                                  CH.sub.3                                                                             CH.sub.2                                 H   H     F     Cl  CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.3                                                                             CHF                                      H   H     H     H   CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CHCl                                     H   H     H     Cl  CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CHCl                                     H   H     F     Cl  CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.3                                                                             CHCl                                     H   H     F     Cl  CO.sub.2 CH(CH.sub.3)C CH                                                                  CH.sub.3                                                                             CHCl                                     H   H     F     Cl  CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.3                                                                             CHCl                                     ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                          ##STR28##                                                                                      ##STR29##                                                     R.sup.5     R.sup.6    R.sup.7                                                 ______________________________________                                         H           Cl         H                                                       H           Br         H                                                       H           CH.sub.3   H                                                       F           Cl         H                                                       Cl          Cl         H                                                       F           Cl         OCH(CH.sub.3).sub.2                                     F           Cl         OCH.sub.2 C CH                                          F           Cl         OCH(CH.sub.3)C CH                                       F           Cl         OCH.sub.3                                               F           Cl         OCH.sub.2 CH.sub.2 CH.sub.3                             F           Cl         OCH.sub.2 CHCH.sub.2                                    F           Cl         OCH.sub.2 CO.sub.2 CH.sub.3                             F           Cl         OCH.sub.2 CO.sub.2 CH.sub.2 C CH                        F           Cl         OCH.sub.2 CO.sub.2 C.sub.5 H.sub.11                     F           Cl         CN                                                      F           Cl         SCH.sub.3                                               F           Cl         OCH.sub.2 CHCHCO.sub.2 CH.sub.3                         F           Cl         OCH.sub.2 C.sub.6 H.sub.5                               F           Cl                                                                                         ##STR30##                                              F           Cl         SCH(CH.sub.3).sub.2                                     F           Cl         SCH.sub.2 CHCH.sub.2                                    F           Cl         SCH.sub.2 C CH                                          F           Cl         SCH.sub.2 CO.sub.2 H                                    F           Cl         SCH.sub.2 CO.sub.2 CH.sub.3                             F           Cl                                                                                         ##STR31##                                              F           Cl         OCH(CH.sub.3)CHNOCH.sub.3                               F           Cl         SCH.sub.2 CO.sub.2 CH.sub.2 C CH                        F           Cl         OCHF.sub.2                                              F           Cl         OCH.sub.2 C(Cl)CH.sub.2                                 F           Cl         OCF.sub.2 CHFCl                                         F           Cl         NHSO.sub.2 CH.sub.3                                     F           Cl         NHSO.sub.2 CH(CH.sub.3).sub.2                           F           Cl         NHSO.sub.2 NHCH.sub.3                                   F           Cl         NHSO.sub.2 NHCH.sub.2 CH.sub.3                          F           Cl         CO.sub.2 CH(CH.sub.3).sub.2                             F           Cl         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                     F           Cl         CO.sub.2 CH.sub.2 CF.sub.3                              F           Cl         CON(CH.sub.3).sub.2                                     F           Cl         CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                  F           Cl         CO.sub.2 CH(CH.sub.3)CF.sub.3                           F           Cl                                                                                         ##STR32##                                              F           Cl         CO.sub.2 CH(CH.sub.3)CH.sub.2 SCH.sub.3                 Cl          Cl         H                                                       Cl          Cl         OCHF.sub.2                                              Cl          Cl         OCH(CH.sub.3).sub.2                                     Cl          Cl         OCF.sub.2 CHFCl                                         Cl          Cl         OCH.sub.2 C CH                                          F           Cl         OCH.sub.2 P(O)(OC.sub.2 H.sub.5).sub.2                  Cl          Cl         OCH(CH.sub.3)C CH                                       F           Cl         OCH.sub.2 C(O)N(CH.sub.3).sub.2                         F           Cl         O(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                    Cl          Cl         SCH.sub.2 C CH                                          Cl          Cl         SCH.sub.2 CO.sub.2 H                                    Cl          Cl         SCH.sub.2 CO.sub.2 CH.sub.2 C CH                        Cl          Cl         NHSO.sub.2 CH.sub.3                                     F           Cl         NHSO.sub.2 CF.sub.3                                     Cl          Cl         CO.sub.2 CH(CH.sub.3).sub.2                             Cl          Cl         CO.sub.2 CH(CH.sub.3)CH.sub.2 SCH.sub.3                 Cl          Cl         CO.sub.2 CH(CH.sub.3)CF.sub.3                           Cl          Cl         CON(CH.sub.3).sub.2                                     F           Cl         CO.sub.2 CH.sub.2 C CH                                  F           Cl         CO.sub.2 CH(CH.sub.3)C CH                               Cl          Cl         CO.sub.2 CH.sub.2 CF.sub.3                              Cl          Cl         Cl                                                      F           Cl         CO.sub.2 CH(CH.sub.3).sub.2                             F           Cl         CO.sub.2 CH.sub.3                                       F           Cl         CO.sub.2 CH.sub.2 CH.sub.3                              F           Cl         CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                      F           Cl         OCHF.sub.2                                              F           Cl         SCH.sub.2 CO.sub.2 H                                    F           Cl         SCH.sub.2 CO.sub.2 CH.sub.3                             F           Cl         NHSO.sub.2 CH.sub.2 CH.sub.3                            F           Cl         NHSO.sub.2 CH(CH.sub.3).sub.2                           Cl          Cl                                                                                         ##STR33##                                              Cl          Cl         CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                      F           Cl         CHCHCO.sub.2 CH.sub.2 CH.sub.3                          F           CN         CO.sub.2 CH(CH.sub.3).sub.2                             Cl          CN         CO.sub.2 CH(CH.sub.3).sub.2                             F           CN         OCH.sub.2 C CH                                          F           CN         OCH(CH.sub.3).sub.2                                     Cl          CN         OCH(CH.sub.3).sub.2                                     F           CN         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                     Cl          CN         OCH.sub.2 C CH                                          F           CN         OCH(CH.sub.3)C CH                                       F           CN         CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                  F           CN         OCHF.sub.2                                              F           CN         OCH(CH.sub.3).sub.2                                     F           CN         OCF.sub.2 CHF.sub.2                                     F           CN         SCH.sub.2 CO.sub.2 H                                    F           CN         NHSO.sub.2 CH.sub.3                                     F           CN         NHSO.sub.2 CF.sub.3                                     ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                          ##STR34##                                                                                      ##STR35##                                                     R.sup.5                                                                               R.sup.6    R.sup.8  R.sup.9      W                                      ______________________________________                                         F      Cl         H        CH.sub.3     O                                      F      Cl         H        H            O                                      F      Cl         CH.sub.3 CH.sub.3     O                                      F      Cl         CH.sub.3 CH.sub.2 F   O                                      F      CN         CH.sub.3 CH.sub.2 F   O                                      F      Cl         H        CH.sub.2 CH.sub.3                                                                           O                                      F      Cl         H        CH.sub.2 F   O                                      F      Cl         H        CH.sub.2 Cl  O                                      F      Cl         H        CH.sub.2 Br  O                                      F      Br         H        CH.sub.3     O                                      F      CH.sub.3   H        CH.sub.3     O                                      F      OCH.sub.3  H        CH.sub.3     O                                      F      CN         H        CH.sub.3     O                                      F      CF.sub.3   H        CH.sub.3     O                                      F      OCF.sub.2 H                                                                               H        CH.sub.3     O                                      Cl     Cl         H        CH.sub.3     O                                      Cl     CN         H        CH.sub.3     O                                      F      CN         CH.sub.3 CH.sub.3     O                                      F      CN         H        CH.sub.2 F   O                                      F      CN         H        CH.sub.2 Cl  O                                      F      CN         H        CH.sub.2 Br  O                                      F      CN         H        CH(CH.sub.3).sub.2                                                                          O                                      F      CN         H        CH.sub.2 CH.sub.2 Cl                                                                        O                                      F      CN         H        CH.sub.2 CH.sub.3                                                                           O                                      F      CN         H        CH.sub.2 (CH.sub.2).sub.2 F                                                                 O                                      Cl     Br         H        CH.sub.3     O                                      Cl     CH.sub.3   H        CH.sub.3     O                                      Cl     OCH.sub.3  H        CH.sub.3     O                                      Cl     CN         H        CH.sub.3     O                                      Cl     CF.sub.3   H        CH.sub.3     O                                      Cl     OCF.sub.2 H                                                                               H        CH.sub.3     O                                      Cl     Cl         H        CH.sub.2 F   O                                      Cl     Cl         CH.sub.3 CH.sub.2 F   O                                      Cl     Cl         H        CH.sub.2 Cl  O                                      Cl     Cl         H        CH.sub.2 Br  O                                      Cl     Cl         H        CH.sub.2 CH.sub.3                                                                           O                                      Cl     Cl         CH.sub.3 CH.sub.3     O                                      ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                          ##STR36##                                                                                      ##STR37##                                                     R.sup.5   R.sup.6   R.sup.8  R.sup.9  W                                        ______________________________________                                         H         H         H        Cl       S                                        F         Cl        H        Cl       S                                        Cl        Cl        H        Cl       S                                        F         Cl        H        CH.sub.3 S                                        F         Cl        H        CH.sub.2 CH.sub.3                                                                       S                                        H         SCH.sub.3 H        H        S                                        F         Cl        H        Cl       O                                        F         Cl        H        CH.sub.3 O                                        Cl        CN        H        Cl       S                                        Cl        Cl        H        CH.sub.3 S                                        Cl        Cl        H        CH.sub.2 CH.sub.3                                                                       S                                        Cl        Cl        H        Cl       O                                        F         CN        H        CH.sub.3 O                                        F         CN        H        CH.sub.3 S                                        Cl        Cl        H        CH.sub.3 O                                        ______________________________________                                    

                  TABLE 11                                                         ______________________________________                                          ##STR38##                                                                                     ##STR39##                                                      R.sup.5      R.sup.5           W                                               ______________________________________                                         F            H                 S                                               F            CH.sub.3          S                                               F            CH.sub.2 CH.sub.3 S                                               F            CH.sub.2 C CH     S                                               Cl           CH.sub.2 C CH     S                                               F            CH(CH.sub.3)C CH  S                                               F            CH.sub.2 C CH     O                                               Cl           H                 S                                               Cl           CH.sub.3          S                                               Cl           CH.sub.2 CH.sub.3 S                                               Cl           CH.sub.2 C CH     S                                               F            CH.sub.2 OCH.sub.3                                                                               S                                               F            CH.sub.2 CH.sub.2 CH.sub.3                                                                       S                                               Cl           CH(CH.sub.3)C CH  S                                               F            CH(CH.sub.3).sub.2                                                                               S                                               F            CH.sub.2 CHCH.sub.2                                                                              S                                               Cl           CH.sub.2 CHCH.sub.2                                                                              S                                               F            CF.sub.2 CHF.sub.2                                                                               S                                               Cl           CH.sub.2 C CH     O                                               Cl           CH(CH.sub.3).sub.2                                                                               S                                               Cl           CH.sub.2 CH.sub.2 CH.sub.3                                                                       S                                               Cl           CF.sub.2 CHF.sub.2                                                                               S                                               F            CH.sub.2 CHCHCH.sub.3                                                                            S                                               ______________________________________                                    

                  TABLE 12                                                         ______________________________________                                          ##STR40##                                                                                     ##STR41##                                                      R.sup.5 R.sup.8  R.sup.9  R.sup.10     W                                       ______________________________________                                         H       H        H        H            O                                       F       H        H        CH.sub.3     O                                       F       H        H        CH.sub.2 C CH                                                                               O                                       F       H        H        CH(CH.sub.3)C CH                                                                            O                                       Cl      H        H        CH.sub.2 C CH                                                                               O                                       F       CH.sub.3 H        CH.sub.2 C CH                                                                               O                                       F       H        H        CH.sub.2 C CH                                                                               S                                       Cl      H        H        CH.sub.3     O                                       F       H        H        CH.sub.2 CH.sub.3                                                                           O                                       F       H        H        CH.sub.2 CH.sub.2 CH.sub.3                                                                  O                                       F       H        H        CH(CH.sub.3).sub.2                                                                          O                                       F       H        H        CH.sub.2 CHCH                                                                               O                                       Cl      H        H        CH(CH.sub.3)C CH                                                                            O                                       Cl      H        H        CH.sub.2 C CH                                                                               S                                       F       CH.sub.3 CH.sub.3 CH.sub.2 C CH                                                                               O                                       F       H        H        H            O                                       Cl      H        H        CH.sub.2 CH.sub.3                                                                           O                                       Cl      H        H        CH(CH.sub.3).sub.2                                                                          O                                       Cl      CH.sub.3 H        CH.sub.2 CHCH.sub.2                                                                         O                                       F       CH.sub.3 H        CH.sub.2 C CH                                                                               O                                       Cl      CH.sub.3 CH.sub.3 CH.sub.2 C CH                                                                               O                                       Cl      CH.sub.3 CH.sub.3 CH.sub.2 CHCH.sub.2                                                                         O                                       Cl      H        H        CH.sub.2 CH.sub.2 CH.sub.3                                                                  O                                       Cl      CH.sub.3 H        CH.sub.2 C CH                                                                               O                                       ______________________________________                                    

                  TABLE 13                                                         ______________________________________                                          ##STR42##                                                                                     ##STR43##                                                      R.sup.5         R.sup.8     R.sup.9                                            ______________________________________                                         H               F           F                                                  F               F           F                                                  F               H           H                                                  ______________________________________                                    

                  TABLE 14                                                         ______________________________________                                          ##STR44##                                                                                      ##STR45##                                                     R.sup.5  R.sup.6  R.sup.7          R.sup.8                                     ______________________________________                                         H        H        CO.sub.2 CH.sub.3                                                                               H                                           H        H        CO.sub.2 CH.sub.3                                                                               CH.sub.3                                    H        H        CO.sub.2 C.sub.2 H.sub.5                                                                        CH.sub.3                                    H        H        CO.sub.2 C.sub.2 H.sub.5                                                                        H                                           H        H        CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              CH.sub.3                                    H        H        CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              H                                           H        H        CO.sub.2 CH.sub.2 C CH                                                                          CH.sub.3                                    H        Cl       CO.sub.2 CH.sub.3                                                                               CH.sub.3                                    H        Cl       CO.sub.2 C.sub.2 H.sub.5                                                                        CH.sub.3                                    H        Cl       CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              CH.sub.3                                    H        Cl       CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              CH.sub.3                                    H        Cl       CO.sub.2 CH.sub.2 C CH                                                                          CH.sub.3                                    F        Cl       CO.sub.2 CH.sub.3                                                                               CH.sub.3                                    F        Cl       CO.sub.2 C.sub.2 H.sub.5                                                                        CH.sub.3                                    F        Cl       CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              CH.sub.3                                    F        Cl       CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              H                                           F        Cl       CO.sub.2 CH.sub.2 C CH                                                                          CH.sub.3                                    F        Cl       CO.sub.2 CH(CH.sub.3)C CH                                                                       CH.sub.3                                    F        Cl       CO.sub.2 CH.sub.2 CHCH.sub.2                                                                    CH.sub.3                                    F        Cl       CO.sub.2 CH(CH.sub.3).sub.2                                                                     CH.sub.3                                    F        Cl       CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                              CH.sub.3                                    F        Cl       CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                          CH.sub.3                                    Cl       Cl       CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              CH.sub.3                                    Cl       Cl       CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                              CH.sub.3                                    Cl       Cl       CO.sub.2 CH(CH.sub.3).sub.2                                                                     CH.sub.3                                    Cl       Cl       CO.sub.2 CH.sub.3                                                                               CH.sub.3                                    Cl       Cl       CO.sub.2 CH.sub.2 CH.sub.3                                                                      CH.sub.3                                    F        CN       CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                              CH.sub.3                                    Cl       Cl       CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                              H                                           F        CN       CO.sub.2 CH.sub.3                                                                               CH.sub.3                                    F        CN       CO.sub.2 CH.sub.2 CH.sub.3                                                                      CH.sub.3                                    Cl       CN       CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                              CH.sub.3                                    Cl       Cl       CO.sub.2 CH.sub.2 C CH                                                                          CH.sub.3                                    Cl       CN       CO.sub.2 CH.sub.2 C CH                                                                          CH.sub.3                                    Cl       CN       CO.sub.2 CH(CH.sub.3)C CH                                                                       CH.sub.3                                    Cl       Cl       CO.sub.2 CH.sub.2 CHCH.sub.2                                                                    CH.sub.3                                    Cl       Cl       CO.sub.2 CH(CH.sub.3)C CH                                                                       CH.sub.3                                    ______________________________________                                    

Formulations

Practical formulations of compounds of Formula I can be manufactured in a conventional manner, namely as powders, granules, pellets, solutions, suspensions, emulsions, wettable powders and emulsifiable concentrates, etc. Many of these formulations can be used directly. Sprayable preparations can be diluted with suitable media and sprayed in quantifies of a few to several hundred liters per hectare. Highly concentrated preparations are mainly used as intermediate products for further formulations. The formulations contain roughly between 0.1 and 99% by weight of active substance(s) and at least one carrier from the group a) 0.1 to 20% surfactant substances and b) about 1 to 99.9% solid or liquid diluents. More precisely, they contain these constituents in approximately the quantities stated below, where the formulations can be mixed with further active substances or additives.

    ______________________________________                                                      Weight-%*                                                                      Active                                                                         substance                                                                               Diluent  Surfactant                                      ______________________________________                                         Wettable powders                                                                              20-90      0-74     1-10                                        Suspensions in oil,                                                                           3-50       40-95    0-15                                        emulsions, solutions                                                           (including                                                                     emulsifiable                                                                   concentrates)                                                                  Aqueous suspensions                                                                           10-50      40-84    1-20                                        Dry powders    1-25       70-99    0-5                                         Granules and pellets                                                                          0.1-95     5-99.9   0-15                                        Highly concentrated                                                                           90-99      0-10     0-2                                         preparations                                                                   ______________________________________                                          *Active substance plus a carrier comprising at least one surfactant and/o      diluent = 100 weight%.                                                   

Lower or higher active substance contents can of course be present, depending on the anticipated use and the physical properties of the compound. Higher quantity ratios of surfactant component to active substance are sometimes desirable and are attained by incorporation into the formulation or by mixing in the container.

Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey, though other mined or industrially prepared solid substances can also be used. The more absorbant diluents are preferred for wettable powders whilst the denser diluents are preferred for dry powders. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, (1950) and are preferred for concentrated suspensions under 0.1%. Concentrated solutions are preferably resistant to phase separation at 0° C. Lists of surfactant substances and applications recommended for these are contained in McCutchen's Detergents and Emulsifiers Annual, MC Publishing. Corp., Ridgewood, N. J. and in Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publishing Co. Inc., New York, (1964). All formulations may contain small quantities of additives for reducing frothing, agglomeration, corrosion and growth of microorganisms etc.

The methods for preparation of such products are well known. Solutions are prepared by simply mixing the ingredients. Finely powdered solid preparations are obtained by mixing and, usually, by grinding, for example in a hammer mill or jet mill. Suspensions axe obtained by wet grinding (see for example Littler, U.S. Pat. No. 3,060,084). Granules and pellets can be prepared by spraying the active substance onto preformed granular carriers or by agglomerating them. For these see J. E Browning, Agglomeration, Chemical Engineering, Dec. 4, (1967), p 147 ff. and Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York, (1973), pp 8-57 ff.

For further information on formulation technology see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, 15 Feb. 1966, column 6, line 16 to column 7, line 19 and Examples 10 to 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, 14 Mar. 1967, column 5, line 43 to column 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, 23 Jun. 1959, column 3, line 66 to column 5, line 17 and Examples 1-4;

G. C. Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, (1961), pp 81-96 and

J. D. Fryer and S. A. Evans, Weed Control Handbook, 5th Ed., Blackwell

Scientific Publications, Oxford, (1968), pp 101-103.

Unless stated otherwise, ihe figures given in the following Examples are parts by weight.

EXAMPLE A

    ______________________________________                                         Wettable powder                                                                ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          80%                                                    1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Sodium alkylnaphthalenesulfonate                                                                        2%                                                    Sodium ligninsulfonate   2%                                                    Synthetic amorphous silicic acid                                                                        3%                                                    Kaolinite                13%                                                   ______________________________________                                    

The ingredients are mixed together and ground in a hammer mill until all the solids essentially have a particle size of less than 50 μm, after which they are mixed again and packed.

EXAMPLE B

    ______________________________________                                         Wettable powder                                                                ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          50%                                                    1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Sodium alkylnaphthalenesulfonate                                                                         2%                                                   Low-viscosity methylcellulose                                                                            2%                                                   Diatomic earth           46%                                                   ______________________________________                                    

The ingredients are mixed, coarsely ground in a hammer mill and then ground in a jet mill so that practically all particles have a diameter of less than 10 μm. The product is then mixed again before packing.

EXAMPLE C

    ______________________________________                                         Granulate                                                                      ______________________________________                                         Wettable powder of Example B                                                                         5%                                                       Attapulgite granulate                                                                               95%                                                       (USS 20-40 mesh; 0.84-0.42 mm)                                                 ______________________________________                                    

A slurry of wettable powder with 25 % solid substances is sprayed into a double cone mixer and the granules are then dried and packed.

EXAMPLE D

    ______________________________________                                         Extrusion-pressed pellets                                                      ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          25%                                                    1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Anhydrous sodium sulfate 10%                                                   Crude calcium ligninsulfonate                                                                            5%                                                   Sodium alkylnaphthalenesulfonate                                                                         1%                                                   Calcium/magnesium bentonite                                                                             59%                                                   ______________________________________                                    

The ingredients are mixed together, ground in a hammer mill and then moistened with about 12% water. The mixture is extrusion-pressed into cylinders with a diameter of about 3 mm which are then cut up into pellets of a length of about 3 mm. These can be used directly after drying; however, the dried pellets can be ground up so that the ground particles pass through a USS No. 20 sieve (mesh diameter 0.84 mm). The granules remaining on a sieve of USS No. 40 (mesh diameter 0.42 mm) can be packed for use, whilst the fine particles are recycled.

EXAMPLE E

    ______________________________________                                         Granulate of low tensile strength                                              ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          1%                                                     1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               N,N-Dimethylformamide    9%                                                    Attapulgite granulate (USS sieves 20 to 40)                                                             90%                                                   ______________________________________                                    

The active substance is dissolved in the solvent and the solution is sprayed on to dust-free granules in a double-cone mixer. After spraying of the solution the mixer is left running for a further short time, after which the granules are packed.

EXAMPLE F

    ______________________________________                                         Granulate                                                                      ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                             80%                                                 1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Wetting agent                1%                                                Crude ligninsulfonate (with 5-20% of the natural sugars)                                                   10%                                                Attapulgite clay             9%                                                ______________________________________                                    

The ingredients are mixed and ground until they pass through a 100-mesh sieve. This material is then put in a fluid bed granulator, where the airflow is adusted so that the material is easily whirled up and a free water jet is sprayed on to the whirled up material. Fluidisation and spraying are continued until granules of the desired size are obtained. Spraying is then stopped, but fluidisation is continued, optionally with heating, until the water content has fallen to the desired level, which is generally below 1%. The material is then drawn off and the desired granule size range (usually 1410 to 149 μm) is obtained by sieving on 14- to 100-mesh sieves, after which the granules are packed for use.

EXAMPLE G

    ______________________________________                                         Aqueous suspension                                                             ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          40.0%                                                  1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Polyacrylic acid-based thickener                                                                        0.3%                                                  Dodecylphenol polyethylene glycol ether                                                                 0.5%                                                  Disodium phosphate       1.0%                                                  Monosodium phosphate     0.5%                                                  Polyvinyl alcohol        1.0%                                                  Water                    56.7%                                                 ______________________________________                                    

The ingredients are mixed and ground together in a sand mill to obtain particles essentially of a size of less than 5 μm.

EXAMPLE H

    ______________________________________                                         Strong concentrate                                                             ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          99.0%                                                  1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Silicic acid-Aerogel     0.5%                                                  Synthetic amorphous silicic acid                                                                        0.5%                                                  ______________________________________                                    

The ingredients are mixed and ground in a hammer mill to obtain material that passes through a USS sieve No. 50 (0.3 mm aperture). The concentrate may if necessary also contain further ingredients.

EXAMPLE I

    ______________________________________                                         Wettable powder                                                                ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          90.0%                                                  1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Dioctylsodium sulphosuccinate                                                                           0.1%                                                  Synthetic fine silicic acid                                                                             9.9%                                                  ______________________________________                                    

The ingredients are mixed and ground in a hammer mill to obtain particles essentially of a size of less than 100 μm. The material is sieved through a USS No. 50 sieve and then packed.

EXAMPLE J

    ______________________________________                                         Wettable powder                                                                ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          40%                                                    1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Sodium ligninsulfonate   20%                                                   Montmorillonite clay     40%                                                   ______________________________________                                    

The ingredients are thoroughly mixed, coarsely ground in a hammer mill, then ground in an air-jet mill to obtain particles essentially of a size of less than 10 μm and then mixed again and packed.

EXAMPLE K

    ______________________________________                                         Suspension in oil                                                              ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          35%                                                    1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Mixture of polyalcohol carboxylic acid esters                                                            6%                                                   and oil-soluble petroleum sulfonates                                           Xylene                   59%                                                   ______________________________________                                    

The ingredients are mixed and ground in a sand mill to obtain particles essentially of a size of less than 5 μm. The product can be used as it is or diluted with off or emulsified in water.

EXAMPLE L

    ______________________________________                                         Fine powder                                                                    ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          10%                                                    1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Attapulgite              10%                                                   Pyrophyllite             80%                                                   ______________________________________                                    

The active substance is mixed with attapulgite and then passed through a hammer mill to obtain particles of essentially less than 200 μm in diameter. The ground concentrate is then mixed with the powdered pyrophyllite until a homogeneous mixture is obtained.

EXAMPLE M

    ______________________________________                                         Suspension in oil                                                              ______________________________________                                         1- (2,4-Dichlorophenyl)imino!dihydro-1H,3H,5H-                                                          25%                                                    1,3,4!thiadiazolo 3,4-c!- 1,3,4!oxadiazin-3-one                               Polyoxyethylene sorbitol hexaoleate                                                                      5%                                                   High molecular weight aliphatic hydrocarbon oil                                                         70%                                                   ______________________________________                                    

The ingredients are ground together in a sand mill until the .size of the solid particles is below about 5 μm. The resultant thick suspension can be used as it is, though it is preferably used after dilution with oils or after emulsification in water.

Application

The compounds of the invention are active weedkillers. They are used for wide-range weed control in the pre- and/or post-germination period in areas in which complete control of all vegetation is desirable, such as, for example, around industrial plants, warehouses, car parks, reclaimed land, fenced areas, roads and railway lines. Some of these compounds are used for selective weed control in crops such as rice, wheat, oats, maize, soybeans, sugar-beet, cotton and groundnuts. The compounds of the invention are active weedkillers for selective and/or general weed control of dicotyledonous weeds and grasses in all plantation crops, including coffee, cocoa, sugar cane, oil palms, robber, citrus fruits, grapes, fruit trees, nut trees, bananas, plantain, pineapples and conifers such as Scots and other pines and spruces.

The compounds can be used in the pre- and/or post-germination period using techniques such as `banding`, direct spraying or broadcast sowing. The applied quantities are determined by a number of factors, including whether they are used as general herbicides, the environment in which they are used, the crop being treated, the types of weeds to be controlled, the weather at the time and the climate in general, the choice of formulation, the method of application, foliage stage, and the like. The quantity of the compounds of the invention that appears optimum to the expert can thus be selected for use in areas where complete control of the entire vegetation is desirable, such as, for example, around storage tanks, industrial plants, advertising areas, roads; railway lines, and fencing. Alternatively, when the correct quantities have been selected for application, the compounds of the invention can be used for selective weed control in plantations for groundnuts, citrus fruits, sugar cane, coffee, oil palms, robber, cocoa, grapes, fruit trees, nut trees, pineapples and bananas. The compounds in question are generally applied in quantities of between 0.001 to 20 kg/hectare, the preferred application quantity being 0.01 to 2 kg/hectare.

The compounds of the invention can be used in combination with other herbicides which are listed below. They are particularly useful in combination with triazines, triazoles, uracils, ureas, amides, carbamates, bipyridyl and phenoxy compounds, sulphone ureas and imidazoles for total control of vegetation in plantation and other crops. The compounds can also be used in combination with mefluidide, glyphosate or gluphosinate.

A mixture of one or more of the following herbicides with a compound of the invention can be particularly useful for weed control. Examples of other herbicides with which the compounds of the invention can be formulated are: .

Acetochlor, acifluorfen, acrolein, 2-propenal, alachior, ametryn, amidosulfuron, ammonium sulfamate, amitroles, Anilofos, asulam, atrazines, Barban, Benefin, bensulfuron methyl, bensulides, bentazone, benzofluorine, Benzoylprop, Bifenox, bromacil, bromoxynil, bromoxynil heptanoate and octanoate, butachlor, buthidazoles, butraline, butylates, cacodylic acid, 2-chloro-N,N-di-2-propenyl-acetamide, 2-chloroallyldiethyldithiocarbamate, Chloramben, chlorbromuron, chloridazon, chlorimuron ethyl, chlormethoxynil, chlomitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, Clethodium, clomazone, cloproxydim, clopyralid, methylarsonic acid or the corresponding calcium salt, cyanazines, cycloates, cyluron, Cyperquat, cyprazines, cyprazoles, cypromid, Delapon, dazomate, dimethyl 2,3,5,6-tetrachloro-1,4-dibenzenedicarboxylate, Desmedipham, Desmetryn, Dicamba, dichlobenil, dichlorprop, Diclofop, diethatyl, Difenzoquat, diflufenican, dimepiperates, dinitramines, Dinoseb, diphenamid, Dipropetryn, Diquat, diuron, 2-methyl-4,6-dinitrophenol, methylarsonic acid disodium salt, Dymron, Endothall, S-ethyldipropylcarbamothioate, Esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, Fenac, Fenoxaprop, fenuron, fenuron trichloroacetate, Flameprop, Fluazifop, Fluazifop-P, fluchloralin, Flumesulam, Flumipropyn, fluometuron, fluorochloridone, fluorodifen, fluoroglycofen, flupoxam, fluridones, Fluroxypyr, fluzasulfuron, Fomasafen, fosamines, glyphosates, Haloxyfop, hexaflurates, hexazinones, imazamethabenz, Imazethapyr, imazosulfuron, Ioxynil, isopropalin, isoproturon, isottron, isoxaben, karbutilate, lactofen, Lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium methylarsonate, (4-chloro-2-methylphenoxy)acetic acid, S,S'-dimethyl-2-(difluoromethyl))-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, Mecoprop, Mefenacet, mefluidides, methalpropalin, methabenzthiazttron, Metham, methazoles, methoxuron, Metolachlor, Metribuzin, 1,2-dihydropyridazine-3,6-dione, molinates, monolinuron, monuron, monuron trichloroacetate, monososodium methylarsonate, napropamides, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorofen, Norea, norflurazon, oryzalin, oxadiazon, oxyflorofen, Paraquat, pebulates, pendimethalin, perfluidone, phenmedipham, picloram, 5- 2-chloro-4-(trifluoromethyl)phenoxy!-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazines, profluralin, prometon, Prometryn, pronamides, propachlor, propanil, propazines, Propham, prosulfalin, Prynachlor, pyrazolates, pyrazon, pyrazosulfuron ethyl, Quinchlorac, Quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazines, 1-(α,α-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazines, terbutol, Terbutryn, thifensulfuron methyl, thiobencarb, triallates, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphans, trifluralin, trimeturon, (2,4-dichlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butyric acid, vemolates and xylachlor. Results for Tests A-D are given in Tables A-D.

                  INDEX TABLE A                                                    ______________________________________                                          ##STR46##                                                                     Cmpd #  R.sup.5 R.sup.7          mp.sup.a                                      ______________________________________                                         1       H       H                oil                                           2       Cl      H                oil                                           3       Cl      Cl               oil                                           9       F       CO.sub.2 CH(CH.sub.3).sub.2                                                                     118-119° C.                            10      f       OCH2CHCH2        119° C.                                11      F       OCH.sub.2 C CH   194° C.                                12      F       OCH.sub.2 -cyclopropyl                                                                          104° C.                                13      F       OCH(CH.sub.3)C CH                                                                               108° C.                                14      F       OCH(CH.sub.3).sub.2                                                                             129° C.                                15      F       OCH.sub.2 Ph     126° F.                                16      F       OCH.sub.2 CHCHCO.sub.2 CH.sub.3                                                                 119-121° C.                            ______________________________________                                          ##STR47##                                                                      ##STR48##                                                                      ##STR49##                                                                      ##STR50##                                                                      .sup.a1 H NMR data for oils are given in Index Table B.                  

    ______________________________________                                         INDEX TABLE B                                                                  Cmpd No.                                                                              .sup.1 H NMR Data.sup.a                                                 ______________________________________                                         1      Me.sub.2 SO-d.sub.6                                                                       4.11(t,2H), 4.50(t,2H), 5.18(s,2H), 6.98                                       (d,2H), 7.37(d,2H).                                          2      Me.sub.2 SO-d.sub.6                                                                       Two isomers: 3.82 and 4.01(2t,2H), 4.12                                        and 4.53(2t,2H), 5.17 and 5.22(2s,2H),                                         7.10(2d,1H), 7.30-7.35(m,1H), 7.50                                             and 7.56(2d,1H).                                             3      CDCl.sub.3 3.85(t,2H), 4.05(t,2H), 5.16(s,2H), 7.07                                       (s,1H), 7.53(s,1H).                                          5      CDCl.sub.3 1.85-1.98(m,1H), 2.08-2.22(m,1h),                                              2.22-2.37(m,2H), 3.55-3.65(m,1H),                                              4.00-4.11(m,1H), 4.54(dd,1H), 6.84                                             (d,1H), 7.17(d,1H), 7.40(s,1H).                              6      CDCl.sub.3 1.85-1.95(m,1H), 2.08-2.19(m,1H),                                              2.20-2.35(m,2H), 3.51-3.61(m,1H),                                              3.95-4.08(m,1H), 4.52(dd,1H), 7.01                                             (s,1H), 7.43(s,1H).                                          7      CDCl.sub.3 1.85-1.98(m,1H), 2.08-2.22(m,1h),                                              2.22-2.37(m,2H), 3.55-3.65(m,1H),                                              4.00-4.11(m,1H), 4.54(dd,1H), 6.84                                             (d,1H), 7.17(d,1H), 7.40(s,1H).                              ______________________________________                                          .sup.a 1 H NMR data are in ppm downfield from tetramethylsilane and were       measured at 500 MHz. Couplings are designated by ssinglet, ddoublet,           ttriplet, mmultiplet, dddoublet of doublets.                             

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine ), blackgrass (Alopecurus myosur oides ), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza saliva), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonurn convolvulus), wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                                      TABLE A                                      __________________________________________________________________________              COMPOUND            COMPOUND                                          Rate 1000 g/ha                                                                          2 3 5 6 7  Rate 1000 g/ha                                                                          2 3 5 6 7                                         __________________________________________________________________________     Postemergence       Preemergence                                               Barley   3 2 2 2 3  Barley   0 0 0 0 0                                         Barnyardgrass                                                                           8 4 4 4 5  Barnyardgrass                                                                           7 0 0 0 0                                         Bedstraw 7 5 5 6 3  Bedstraw 7 0 2 0 --                                        Blackgrass                                                                              2 2 2 1 2  Blackgrass                                                                              1 0 0 0 0                                         Cheatgrass                                                                              --                                                                               --                                                                               --                                                                               --                                                                               -- Cheatgrass                                                                              --                                                                               --                                                                               --                                                                               --                                                                               --                                        Chickweed                                                                               2 2 1 0 0  Chickweed                                                                               0 0 2 0 0                                         Cocklebur                                                                               7 4 5 6 6  Cocklebur                                                                               0 0 0 0 0                                         Corn     3 3 2 2 3  Corn     3 0 0 0 0                                         Cotton   10                                                                               9 10                                                                               9 9  Cotton   2 2 0 0 0                                         Crabgrass                                                                               5 3 3 3 4  Crabgrass                                                                               8 3 0 0 0                                         Downy brome                                                                             3 0 3 1 1  Downy brome                                                                             1 0 0 0 0                                         Giant foxtail                                                                           5 2 3 4 3  Giant foxtail                                                                           7 3 0 0 0                                         Morningglory                                                                            8 7 6 9 8  Morningglory                                                                            0 0 0 0 0                                         Nutsedge 7 --                                                                               0 0 6  Nutsedge 0 8 0 0 0                                         Rape     8 5 9 5 3  Rape     10                                                                               8 0 0 0                                         Rice     3 3 3 0 2  Rice     0 0 0 0 0                                         Sorghum  4 3 4 3 4  Sorghum  2 0 0 0 0                                         Soybean  8 3 4 3 6  Soybean  0 0 0 0 0                                         Sugarbeet                                                                               9 6 8 10                                                                               9  Sugarbeet                                                                               4 2 0 0 0                                         Velvetleaf                                                                              10                                                                               9 8 9 10 Velvetleaf                                                                              10                                                                               10                                                                               0 0 0                                         Wheat    3 1 2 1 2  Wheat    0 0 0 0 0                                         Wild buckwheat                                                                          9 8 10                                                                               10                                                                               9  Wild buckwheat                                                                          9 2 0 0 0                                         Wild oat 2 0 2 2 2  Wild oat 3 0 0 0 0                                         __________________________________________________________________________             COMPOUND                                                               Rate 200 g/ha                                                                          1 2 3 4 5 6 7 8 9 10                                                                               11                                                                               12                                                                               13                                                                               14                                                                               15                                                                               16                                       __________________________________________________________________________     Postemergence                                                                  Barley  3 3 0 5 2 2 2 5 8 7 9 7 8 8 3 9                                        Barnyardgrass                                                                          5 5 3 9 2 2 3 7 10                                                                               9 9 9 10                                                                               10                                                                               5 9                                        Bedstraw                                                                               5 6 5 10                                                                               3 3 3 10                                                                               10                                                                               10                                                                               10                                                                               9 10                                                                               10                                                                               9 10                                       Blackgrass                                                                             2 1 0 7 2 1 1 4 9 8 9 8 9 8 4 4                                        Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               9 8 3 4                                        Chickweed                                                                              2 1 0 10                                                                               0 0 0 10                                                                               10                                                                               10                                                                               10                                                                               8 10                                                                               8 7 6                                        Cocklebur                                                                              6 6 5 10                                                                               6 5 5 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Corn    3 3 2 7 2 2 2 2 8 8 9 8 8 9 2 4                                        Cotton  9 10                                                                               9 10                                                                               9 8 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Crabgrass                                                                              5 2 3 --                                                                               2 3 2 7 8 9 9 9 9 9 7 4                                        Downy brome                                                                            3 3 1 5 1 0 0 4 6 8 8 6 --                                                                               --                                                                               --                                                                               --                                       Giant foxtail                                                                          4 4 3 9 2 1 2 6 8 9 9 9 9 9 6 6                                        Morningglory                                                                           8 7 6 10                                                                               5 6 7 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9                                        Nutsedge                                                                               2 --                                                                               6 5 0 4 0 0 4 6 7 3 4 7 1 1                                        Rape    2 7 4 10                                                                               4 2 1 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Rice    3 2 2 9 1 0 0 4 10                                                                               9 9 9 10                                                                               9 4 4                                        Sorghum 4 3 2 8 3 3 3 6 9 9 9 9 9 9 4 7                                        Soybean 5 3 3 10                                                                               3 3 3 10                                                                               9 9 10                                                                               9 10                                                                               10                                                                               8 9                                        Sugarbeet                                                                              3 4 3 10                                                                               5 6 7 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Velvetleaf                                                                             9 9 9 10                                                                               8 7 6 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Wheat   1 1 0 7 0 0 1 5 6 8 9 8 9 9 4 9                                        Wild buckwheat                                                                         6 8 9 10                                                                               7 8 7 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Wild oat                                                                               2 2 0 7 1 0 1 5 7 8 9 7 9 8 3 8                                        Preemergence                                                                   Barley  0 0 0 6 0 0 0 0 6 5 6 2 6 2 0 1                                        Barnyardgrass                                                                          0 0 0 8 0 0 0 0 9 9 9 9 9 10                                                                               3 6                                        Bedstraw                                                                               0 2 0 10                                                                               --                                                                               --                                                                               0 3 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Blackgrass                                                                             0 0 0 6 0 0 0 7 7 4 6 4 7 8 3 1                                        Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               6 8 3 1                                        Chickweed                                                                              0 0 0 10                                                                               0 0 0 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 6 0                                        Cocklebur                                                                              0 0 0 10                                                                               0 0 0 3 10                                                                               10                                                                               10                                                                               9 10                                                                               9 8 8                                        Corn    0 0 0 4 0 0 0 0 6 7 8 2 6 6 2 1                                        Cotton  0 0 0 8 0 0 0 0 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               7 10                                       Crabgrass                                                                              4 3 2 9 0 0 0 0 9 10                                                                               10                                                                               9 10                                                                               10                                                                               8 4                                        Downy brome                                                                            0 0 0 3 0 0 0 0 5 6 7 6 --                                                                               --                                                                               --                                                                               --                                       Giant foxtail                                                                          0 2 0 9 0 0 0 0 10                                                                               10                                                                               10                                                                               8 9 10                                                                               5 3                                        Morningglory                                                                           0 0 0 10                                                                               0 0 0 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               7                                        Nutsedge                                                                               --                                                                               0 0 0 0 --                                                                               0 --                                                                               --                                                                               10                                                                               7 9 4 7 9 8                                        Rape    0 2 0 10                                                                               0 0 0 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               8 10                                       Rice    0 0 0 3 0 0 0 0 6 7 8 3 9 9 0 3                                        Sorghum 0 0 0 3 0 0 0 0 4 6 7 5 9 9 0 2                                        Soybean 0 0 0 10                                                                               0 0 0 0 8 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               2 2                                        Sugarbeet                                                                              0 0 0 10                                                                               0 0 0 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Velvetleaf                                                                             10                                                                               8 7 10                                                                               0 0 0 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                       Wheat   0 0 0 7 0 0 0 2 6 3 7 3 7 6 1 2                                        Wild buckwheat                                                                         0 0 1 10                                                                               0 0 0 2 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               7 6                                        Wild oat                                                                               0 0 0 8 0 0 0 4 7 7 9 6 9 8 3 0                                        __________________________________________________________________________             COMPOUND                                                               Rate 50 g/ha                                                                           1 4   8 9   10                                                                               11  12                                                                               13  14                                                                               15  16                                       __________________________________________________________________________     Postemergence                                                                  Barley  2 4   4 5   6 7   4 6   4 5   5                                        Barnyardgrass                                                                          3 6   6 8   9 9   9 9   9 4   9                                        Bedstraw                                                                               3 10  10                                                                               10  10                                                                               10  9 10  10                                                                               8   9                                        Blackgrass                                                                             1 3   4 6   6 8   4 7   6 3   3                                        Cheatgrass                                                                             --                                                                               --  --                                                                               --  --                                                                               --  --                                                                               7   4 3   3                                        Chickweed                                                                              2 10  10                                                                               9   8 10  7 9   4 4   6                                        Cocklebur                                                                              6 10  10                                                                               10  10                                                                               10  10                                                                               10  9 9   10                                       Corn    3 5   3 5   6 8   5 5   5 2   3                                        Cotton  9 10  10                                                                               10  10                                                                               10  10                                                                               10  10                                                                               10  10                                       Crabgrass                                                                              3 5   6 6   8 9   8 8   8 7   6                                        Downy brome                                                                            3 4   4 5   4 6   4 --  --                                                                               --  --                                       Giant foxtail                                                                          3 6   6 6   7 9   8 7   8 5   8                                        Morningglory                                                                           7 10  10                                                                               10  10                                                                               10  10                                                                               10  10                                                                               9   9                                        Nutsedge                                                                               0 5   3 3   3 6   6 3   7 1   1                                        Rape    2 10  10                                                                               10  10                                                                               10  10                                                                               10  10                                                                               10  10                                       Rice    2 6   3 8   9 9   7 9   9 4   4                                        Sorghum 3 6   4 6   8 9   7 8   9 3   5                                        Soybean 4 8   9 9   9 9   9 10  9 8   8                                        Sugarbeet                                                                              2 10  9 10  10                                                                               10  10                                                                               10  10                                                                               10  10                                       Velvetleaf                                                                             7 10  10                                                                               10  10                                                                               10  10                                                                               10  10                                                                               10  10                                       Wheat   1 7   5 5   6 7   5 6   6 3   6                                        Wild buckwheat                                                                         6 10  10                                                                               10  10                                                                               10  10                                                                               10  10                                                                               10  10                                       Wild oat                                                                               1 5   4 6   6 8   4 7   5 2   8                                        Preemergence                                                                   Barley  0 1   0 1   2 2   2 2   2 0   0                                        Barnyardgrass                                                                          0 3   0 6   7 8   6 8   8 0   3                                        Bedstraw                                                                               0 6   0 10  10                                                                               10  9 10  9 2   0                                        Blackgrass                                                                             0 4   0 4   1 5   1 5   3 0   0                                        Cheatgrass                                                                             --                                                                               --  --                                                                               --  --                                                                               --  --                                                                               3   2 2   0                                        Chickweed                                                                              --                                                                               10  9 8   8 10  4 10  6 2   0                                        Cocklebur                                                                              0 9   0 6   8 10  8 7   9 3   5                                        Corn    0 3   0 2   3 3   1 3   3 1   0                                        Cotton  0 2   0 0   10                                                                               9   2 7   6 0   0                                        Crabgrass                                                                              0 5   0 9   9 10  8 9   9 2   2                                        Downy brome                                                                            0 3   0 3   3 8   3 --  --                                                                               --  --                                       Giant foxtail                                                                          0 5   0 7   8 8   5 6   9 0   3                                        Morningglory                                                                           0 10  7 10  9 10  9 10  10                                                                               4   5                                        Nutsedge                                                                               --                                                                               0   --                                                                               --  7 3   4 3   8 3   3                                        Rape    0 10  2 9   10                                                                               10  7 9   10                                                                               3   3                                        Rice    0 0   0 2   3 5   2 3   5 0   0                                        Sorghum 0 2   0 2   5 4   2 3   5 0   0                                        Soybean 0 6   0 0   8 6   4 5   10                                                                               0   0                                        Sugarbeet                                                                              0 9   8 10  10                                                                               10  10                                                                               10  10                                                                               8   8                                        Velvetleaf                                                                             0 10  3 9   10                                                                               10  10                                                                               10  10                                                                               10  8                                        Wheat   0 5   0 3   3 5   2 4   5 0   0                                        Wild buckwheat                                                                         0 0   0 9   10                                                                               10  5 10  9 3   3                                        Wild oat                                                                               0 7   0 5   6 7   3 6   6 2   0                                        __________________________________________________________________________

TEST B

Seeds of barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria spp.), downy brome (Bromus rectorurn), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), sorghum (Sorghum bicolor), velvetleaf (Abutlion theophrasti), and wild oat (Avenafatua) were planted into a sandy loam soil and treated preemergence, or with a soil drench (PDRN), with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated postemergence, or sprayed to runoff (STRO), with test chemicals. Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table B, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.

                                      TABLE B                                      __________________________________________________________________________             COMPOUND                COMPOUND                                       Rate 2000 g/ha                                                                         1 2 3 4 5 6 7 8 Rate 1000 g/ha                                                                         1 2 3 4 5 6 7 8                                __________________________________________________________________________     Preemergence            Postemergence                                          Barnyardgrass                                                                          8 9 0 9 0 4 0 9 Barnyardgrass                                                                          8 5 4 10                                                                               3 2 3 9                                Cocklebur                                                                              5 4 3 10                                                                               0 0 0 10                                                                               Cocklebur                                                                              7 7 2 10                                                                               4 4 1 10                               Crabgrass                                                                              8 9 7 10                                                                               1 0 0 9 Crabgrass                                                                              8 6 4 10                                                                               3 2 2 10                               Downy brome                                                                            2 0 0 10                                                                               0 0 0 0 Downy brome                                                                            3 2 1 6 1 0 0 4                                Giant foxtail                                                                          9 9 4 10                                                                               3 0 0 9 Giant foxtail                                                                          9 7 3 10                                                                               4 3 3 10                               Morningglory                                                                           3 4 2 10                                                                               0 0 0 10                                                                               Morningglory                                                                           8 9 9 10                                                                               8 9 8 10                               Sorghum 4 8 0 10                                                                               0 0 0 8 Sorghum 3 4 3 9 2 3 3 6                                Velvetleaf                                                                             10                                                                               10                                                                               7 10                                                                               0 0 0 10                                                                               Velvetleaf                                                                             10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                               Wild oats                                                                              0 0 0 10                                                                               0 0 0 7 Wild oats                                                                              2 3 1 9 3 2 2 7                                __________________________________________________________________________

TEST C

The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 era for the flood test and was maintained at this level for the duration of the test. Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeurn vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinaIis), downy brome (Bromus rectorurn), giant foxtail (Setaria faberii), johnsongrass (Sorghum halpense), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lollurn multiflorum), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonurn convolvulus), and wild oat (Avena fatua). All plant species were planted One day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyardgrass (Echinochloa crus-galli) and Late watergrass (Echinocloa oryzicola) grown to the 1 and 2 leaf stage for testing. All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings, summarized in Table C, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

                                      TABLE C                                      __________________________________________________________________________             Compound            Compound                                           Rate 125 g/ha                                                                          9           Rate 125 g/ha                                                                          9                                                  __________________________________________________________________________     Postemergence       Preemergence                                               Barley  30          Barley  50                                                 Barnyardgrass                                                                          95          Barnyardgrass                                                                          100                                                Blackgrass                                                                             80          Blackgrass                                                                             80                                                 Chickweed                                                                              100         Chickweed                                                                              100                                                Cocklebur                                                                              100         Cocklebur                                                                              95                                                 Corn    50          Corn    25                                                 Cotton  100         Cotton  50                                                 Crabgrass                                                                              65          Crabgrass                                                                              95                                                 Downy brome                                                                            35          Downy brome                                                                            0                                                  Duck salad                                                                             20          Galium  55                                                 Galium  100         Giant foxtail                                                                          100                                                Giant foxtail                                                                          95          It. Ryegrass                                                                           85                                                 It. Ryegrass                                                                           80          Johnsongrass                                                                           95                                                 Johnsongrass                                                                           95          Morningglory                                                                           100                                                Morningglory                                                                           100         Rape    50                                                 Rape    100         Redroot pigweed                                                                        100                                                Redroot pigweed                                                                        100         Soybean 100                                                Rice japonica                                                                          100         Speedwell                                                                              100                                                Soybean 100         Sugar beet                                                                             100                                                Speedwell                                                                              100         Velvetleaf                                                                             100                                                Sugar beet                                                                             100         Wheat   0                                                  Umbrella sedge                                                                         90          Wild buckwheat                                                                         100                                                Velvetleaf                                                                             100         Wild oat                                                                               80                                                 Watergrass-2                                                                           100                                                                    Wheat   60                                                                     Wild buckwheat                                                                         100                                                                    Wild oat                                                                               40                                                                     Barnyardgrass-2                                                                        100                                                                    __________________________________________________________________________              Compound                                                              Rate 62 g/ha                                                                            4  8  9  10 11 12 13 14 15 16                                         __________________________________________________________________________     Postemergence                                                                  Barley   35 30 30 40 65 35 60 50 20 30                                         Barnyardgrass                                                                           40 40 90 90 95 95 95 95 10 80                                         Blackgrass                                                                              50 40 70 45 80 50 95 75 40 20                                         Chickweed                                                                               95 95 100                                                                               100                                                                               100                                                                               90 100                                                                               85 75 25                                         Cocklebur                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Corn     25 30 45 35 60 25 55 50 20 30                                         Cotton   100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Crabgrass                                                                               40 20 55 65 80 45 90 85 25 20                                         Downy brome                                                                             50 40 35 35 35 25 50 35 20 0                                          Duck salad                                                                              0  0  20 90 30 50 25 -- 40 0                                          Galium   100                                                                               100                                                                               100                                                                               95 100                                                                               90 100                                                                               90 90 35                                         Giant foxtail                                                                           70 50 85 80 95 90 95 95 35 60                                         It. ryegrass                                                                            50 30 60 70 95 60 95 75 25 0                                          Johnsongrass                                                                            90 50 90 90 95 90 95 90 45 80                                         Morningglory                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                        Rape     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Redroot pigweed                                                                         100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Rice japonica                                                                           95 10 100                                                                               90 95 75 65 -- 40 10                                         Soybean  90 95 95 75 100                                                                               85 100                                                                               90 100                                                                               70                                         Speedwell                                                                               100                                                                               100                                                                               100                                                                               -- 100                                                                               100                                                                               100                                                                               100                                                                               -- 95                                         Sugar beet                                                                              100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Umbrella sedge                                                                          0  0  90 100                                                                               85 100                                                                               80 -- 65 0                                          Velvetleaf                                                                              100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Watergrass-2                                                                            70 10 100                                                                               95 100                                                                               90 95 -- 50 10                                         Wheat    35 30 -- 35 75 40 75 35 40 20                                         Wild buckwheat                                                                          100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               --                                         Wild oat 50 40 40 70 90 40 90 75 25 25                                         Barnyardgrass-2                                                                         10 0  100                                                                               95 100                                                                               85 75 -- 75 10                                         Preemergence                                                                   Barley   0  0  30 30 75 35 60 80 0  0                                          Barnyardgrass                                                                           60 10 100                                                                               95 100                                                                               85 100                                                                               95 20 0                                          Blackgrass                                                                              30 0  55 50 90 85 90 85 20 0                                          Chickweed                                                                               100                                                                               100                                                                               90 65 100                                                                               60 100                                                                               30 10 0                                          Cocklebur                                                                               50 0  85 40 85 80 65 85 10 15                                         Corn     20 10 25 35 60 25 40 30 0  0                                          Cotton   75 10 -- 60 100                                                                               35 90 90 0  10                                         Crabgrass                                                                               55 40 90 90 100                                                                               100                                                                               100                                                                               95 20 0                                          Downy brome                                                                             0  0  0  10 35 10 40 30 10 20                                         Galium   100                                                                               35 40 30 100                                                                               35 100                                                                               70 60 20                                         Giant foxtail                                                                           80 0  100                                                                               95 100                                                                               80 100                                                                               95 10 20                                         It. ryegrass                                                                            55 0  10 70 95 10 95 90 10 20                                         Johnsongrass                                                                            40 0  85 90 90 90 95 95 35 10                                         Morningglory                                                                            100                                                                               90 50 100                                                                               100                                                                               70 100                                                                               95 50 0                                          Rape     100                                                                               30 20 90 100                                                                               20 100                                                                               100                                                                               20 10                                         Redroot pigweed                                                                         100                                                                               85 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               60                                         Soybean  0  40 100                                                                               40 100                                                                               15 60 85 10 15                                         Speedwell                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               50                                         Sugar beet                                                                              95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               50 0                                          Velvetleaf                                                                              100                                                                               40 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               30 0                                          Wheat    0  0  0  30 45 20 50 55 10 0                                          Wild buckwheat                                                                          90 90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 0                                          Wild oat 55 0  60 60 90 40 90 80 10 0                                          __________________________________________________________________________              Compound                                                              Rate 31 g/ha                                                                            4  8  9  10 11 12 13 14 15 16                                         __________________________________________________________________________     Postemergence                                                                  Barley   35 30 30 40 50 30 50 40 20 20                                         Barnyardgrass                                                                           35 30 40 90 85 85 95 95 10 80                                         Blackgrass                                                                              40 30 35 40 80 35 80 65 35 20                                         Chickweed                                                                               80 80 100                                                                               100                                                                               100                                                                               70 100                                                                               70 60 25                                         Cocklebur                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               80                                         Corn     25 25 30 30 35 20 35 35 15 25                                         Cotton   100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Crabgrass                                                                               30 20 55 50 65 40 45 50 20 0                                          Downy brome                                                                             40 30 10 35 30 20 35 35 20 0                                          Duck salad                                                                              0  0  15 85 30 0  0  45 25 0                                          Galium   100                                                                               100                                                                               100                                                                               -- 100                                                                               80 100                                                                               90 85 0                                          Giant foxtail                                                                           50 45 85 70 80 40 90 90 25 40                                         It. ryegrass                                                                            40 25 30 60 90 30 80 70 20 0                                          Johnsongrass                                                                            90 40 45 80 95 50 90 90 30 70                                         Morningglory                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 85                                         Rape     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               50                                         Redroot pigweed                                                                         100                                                                               -- 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               85                                         Rice japonica                                                                           85 10 90 70 70 45 40 65 35 10                                         Soybean  90 95 95 65 95 85 100                                                                               90 55 60                                         Speedwell                                                                               100                                                                               100                                                                               100                                                                               -- 100                                                                               100                                                                               -- 100                                                                               -- 95                                         Sugar beet                                                                              100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Umbrella sedge                                                                          0  0  70 100                                                                               85 85 40 80 0  0                                          Velvetleaf                                                                              100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Watergrass-2                                                                            55 0  90 95 100                                                                               60 70 85 45 10                                         Wheat    30 30 30 35 50 35 60 35 35 20                                         Wild buckwheat                                                                          100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Wild oat 35 30 30 65 90 30 80 70 20 10                                         Barnyardgrass-2                                                                         0  0  100                                                                               90 95 80 60 90 65 10                                         Preemergence                                                                   Barley   0  0  20 20 70 35 40 60 0  0                                          Barnyardgrass                                                                           20 0  95 50 100                                                                               80 95 95 15 0                                          Blackgrass                                                                              20 0  35 35 60 30 70 70 0  0                                          Chickweed                                                                               20 80 80 50 100                                                                               30 75 0  0  0                                          Cocklebur                                                                               20 0  60 35 65 30 35 50 0  10                                         Corn     0  0  20 25 55 25 30 20 -- 0                                          Cotton   40 10 30 50 100                                                                               20 50 60 0  0                                          Crabgrass                                                                               70 20 80 60 100                                                                               55 90 70 10 0                                          Downy brome                                                                             0  0  0  0  10 0  30 10 0  10                                         Galium   70 -- 20 30 100                                                                               10 100                                                                               70 10 0                                          Giant foxtail                                                                           70 0  95 85 100                                                                               60 95 90 0  0                                          It. ryegrass                                                                            0  0  0  30 75 -- 70 20 0  10                                         Johnsongrass                                                                            30 0  50 75 90 40 95 70 15 0                                          Morningglory                                                                            20 20 50 75 100                                                                               50 50 75 20 0                                          Rape     0  0  0  45 100                                                                               -- 90 100                                                                               0  0                                          Redroot pigweed                                                                         100                                                                               50 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 30                                         Soybean  0  20 100                                                                               10 15 10 60 75 0  0                                          Speedwell                                                                               100                                                                               95 100                                                                               60 100                                                                               100                                                                               100                                                                               100                                                                               90 --                                         Sugar beet                                                                              95 0  100                                                                               100                                                                               100                                                                               60 100                                                                               100                                                                               10 0                                          Velvetleaf                                                                              100                                                                               0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               20 0                                          Wheat    0  0  0  20 25 10 30 10 0  0                                          Wild buckwheat                                                                          55 90 100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               30 0                                          Wild oat 25 0  30 30 85 40 50 65 0  0                                          __________________________________________________________________________              Compound                                                              Rate 16 g/ha                                                                            4  8  9  10 11 12 13 14 15 16                                         __________________________________________________________________________     Postemergence                                                                  Barley   30 25 30 35 35 25 40 30 -- 10                                         Barnyardgrass                                                                           30 25 30 30 85 35 70 70 10 65                                         Blackgrass                                                                              40 -- 30 40 55 35 75 60 30 20                                         Chickweed                                                                               70 70 80 90 95 65 90 70 55 25                                         Cocklebur                                                                               90 95 100                                                                               85 100                                                                               95 100                                                                               100                                                                               95 --                                         Corn     20 20 20 25 25 15 20 20 10 25                                         Cotton   100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Crabgrass                                                                               25 15 30 30 45 25 35 45 20 0                                          Downy brome                                                                             30 25 10 30 25 10 30 25 15 0                                          Duck salad                                                                              0  0  10 50 0  0  0  35 0  0                                          Galium   90 95 100                                                                               90 85 80 85 90 65 0                                          Giant foxtail                                                                           45 35 60 55 80 20 80 55 25 40                                         It. ryegrass                                                                            25 20 20 30 35 20 40 35 20 0                                          Johnsongrass                                                                            85 30 40 65 70 35 60 50 25 70                                         Morningglory                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               -- 85                                         Rape     100                                                                               100                                                                               100                                                                               -- 100                                                                               100                                                                               100                                                                               100                                                                               90 40                                         Redroot pigweed                                                                         100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               80                                         Rice japonica                                                                           55 0  50 25 30 30 35 60 20 10                                         Soybean  85 95 85 65 85 75 85 80 55 45                                         Speedwell                                                                               100                                                                               90 100                                                                               -- -- 100                                                                               -- 100                                                                               70 90                                         Sugar beet                                                                              100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               65                                         Umbrella sedge                                                                          0  0  10 90 35 20 0  50 0  0                                          Velvetleaf                                                                              100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                        Watergrass-2                                                                            0  0  55 35 70 30 70 35 25 0                                          Wheat    25 25 20 25 40 35 40 30 35 10                                         Wild buckwheat                                                                          90 80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               85                                         Wild oat 30 30 20 40 55 30 45 40 20 10                                         Barnyardgrass-2                                                                         0  0  95 40 65 20 25 60 50 0                                          Preemergence                                                                   Barley   0  0  0  0  40 20 30 30 0  0                                          Barnyardgrass                                                                           20 0  85 30 65 35 90 50 10 0                                          Blackgrass                                                                              20 0  10 25 40 10 50 50 0  0                                          Chickweed                                                                               20 10 70 35 70 0  -- 0  -- 0                                          Cocklebur                                                                               0  0  35 10 60 20 20 35 0  0                                          Corn     0  0  10 0  25 10 20 0  0  0                                          Cotton   -- 0  25 20 60 15 45 10 0  0                                          Crabgrass                                                                               20 10 30 30 75 35 70 70 10 0                                          Downy brome                                                                             0  0  0  0  0  0  20 0  0  0                                          Galium   0  0  0  10 30 0  100                                                                               30 0  0                                          Giant foxtail                                                                           50 0  90 65 50 50 90 35 0  0                                          It. ryegrass                                                                            0  0  0  10 20 0  50 10 0  0                                          Johnsongrass                                                                            10 0  20 20 65 20 55 35 0  0                                          Morningglory                                                                            0  10 20 30 100                                                                               40 50 30 10 0                                          Rape     0  0  0  10 20 10 85 85 0  0                                          Redroot pigweed                                                                         100                                                                               30 100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               -- 30                                         Soybean  0  -- 35 0  10 0  35 0  0  0                                          Speedwell                                                                               100                                                                               0  100                                                                               40 100                                                                               100                                                                               100                                                                               100                                                                               50 0                                          Sugar beet                                                                              35 0  100                                                                               60 75 0  100                                                                               100                                                                               0  0                                          Velvetleaf                                                                              70 0  55 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               0  0                                          Wheat    0  0  0  0  20 0  20 10 0  0                                          Wild buckwheat                                                                          0  0  50 100                                                                               100                                                                               90 100                                                                               100                                                                               -- 0                                          Wild oat 0  0  10 20 60 35 30 30 0  0                                          __________________________________________________________________________             Compound                                                               Rate 8 g/ha                                                                            4   8  10  11 12  13 14  15 16                                         __________________________________________________________________________     Postemergence                                                                  Barley  25  20 35  25 25  35 25  20 0                                          Barnyardgrass                                                                          30  20 15  40 35  40 50  10 50                                         Blackgrass                                                                             35  25 35  40 35  70 35  25 20                                         Chickweed                                                                              40  60 80  90 55  85 45  50 25                                         Cocklebur                                                                              90  90 85  90 90  95 90  90 65                                         Corn    15  15 25  25 15  20 15  10 10                                         Cotton  100 100                                                                               100 100                                                                               100 100                                                                               100 100                                                                               100                                        Crabgrass                                                                              20  10 20  10 25  30 30  15 0                                          Downy brome                                                                            30  20 25  25 10  30 20  10 0                                          Duck salad                                                                             0   0  40  0  0   0  0   0  0                                          Galium  60  60 75  75 75  70 35  55 0                                          Giant foxtail                                                                          30  35 20  35 20  35 40  25 20                                         It. ryegrass                                                                           20  20 0   30 20  20 20  20 0                                          Johnsongrass                                                                           40  25 65  45 30  25 25  20 60                                         Morningglory                                                                           95  100                                                                               80  100                                                                               90  95 95  90 75                                         Rape    95  100                                                                               100 100                                                                               100 100                                                                               100 90 20                                         Redroot pigweed                                                                        95  90 100 100                                                                               100 100                                                                               90  100                                                                               80                                         Rice japonica                                                                          40  0  15  20 20  30 30  0  0                                          Soybean 50  90 65  80 50  85 80  55 35                                         Speedwell                                                                              100 90 --  -- 100 70 --  50 80                                         Sugar beet                                                                             100 100                                                                               100 100                                                                               100 100                                                                               90  100                                                                               50                                         Umbrella sedge                                                                         0   0  80  20 20  0  40  0  0                                          Velvetleaf                                                                             100 100                                                                               100 100                                                                               100 100                                                                               100 100                                                                               100                                        Watergrass-2                                                                           0   0  30  25 25  45 25  10 0                                          Wheat   20  20 25  25 30  40 20  20 0                                          Wild buckwheat                                                                         75  80 100 100                                                                               100 100                                                                               100 100                                                                               80                                         Wild oat                                                                               30  20 25  45 30  40 30  20 10                                         Barnyardgrass-2                                                                        0   0  25  25 0   20 30  0  0                                          Preemergence                                                                   Barley  0   0  0   20 20  0  0   0  0                                          Barnyardgrass                                                                          10  0  0   35 10  40 30  10 0                                          Blackgrass                                                                             0   0  25  20 10  10 0   0  0                                          Chickweed                                                                              20  0  20  -- 0   30 0   0  0                                          Cocklebur                                                                              0   0  0   25 0   0  15  0  0                                          Corn    0   0  0   25 10  10 0   0  0                                          Cotton  --  0  10  30 10  30 0   0  0                                          Crabgrass                                                                              0   0  10  25 10  40 45  0  0                                          Downy brome                                                                            0   0  0   0  0   0  0   0  0                                          Galium  0   0  10  0  0   0  0   0  0                                          Giant foxtail                                                                          0   0  30  50 50  40 20  0  0                                          It. ryegrass                                                                           0   0  0   0  0   10 0   0  0                                          Johnsongrass                                                                           0   0  0   30 10  20 25  0  0                                          Morningglory                                                                           0   10 10  60 30  20 20  10 0                                          Rape    0   0  0   0  0   10 20  0  0                                          Redroot pigweed                                                                        30  20 80  100                                                                               70  100                                                                               90  65 0                                          Soybean 0   10 0   10 0   10 0   0  0                                          Speedwell                                                                              100 -- --  100                                                                               95  100                                                                               100 -- 0                                          Sugar beet                                                                             35  0  30  55 0   20 0   0  0                                          Velvetleaf                                                                             45  0  20  100                                                                               30  100                                                                               100 0  0                                          Wheat   0   0  0   0  0   0  0   0  0                                          Wild buckwheat                                                                         0   0  100 95 35  90 100 0  0                                          Wild oat                                                                               0   0  10  10 35  20 20  0  0                                          __________________________________________________________________________               Compound            Compound                                         Rate 4 g/ha                                                                              13 14     Rate 4 g/ha                                                                              13 14                                            __________________________________________________________________________     Postemergence       Preemergence                                               Barley    35 20     Barley    0  0                                             Barnyardgrass                                                                            30 15     Barnyardgrass                                                                            30 20                                            Blackgrass                                                                               60 20     Blackgrass                                                                               -- 0                                             Chickweed 85 35     Chickweed -- 0                                             Cocklebur 90 90     Cocklebur 0  0                                             Corn      20 10     Corn      10 0                                             Cotton    100                                                                               100    Cotton    10 0                                             Crabgrass 20 20     Crabgrass 0  20                                            Downy brome                                                                              20 10     Downy brome                                                                              0  0                                             Duck salad                                                                               -- 0      Galium    9  0                                             Galium    50 30     Giant foxtail                                                                            35 0                                             Giant foxtail                                                                            25 35     It. ryegrass                                                                             10 0                                             It. ryegrass                                                                             20 10     Johnsongrass                                                                             10 0                                             Johnsongrass                                                                             25 20     Morningglory                                                                             10 0                                             Morningglory                                                                             90 90     Rape      0  0                                             Rape      100                                                                               95     Redroot pigweed                                                                          95 30                                            Redroot pigweed                                                                          100                                                                               90     Soybean   0  0                                             Rice japonica                                                                            -- 0      Speedwell 100                                                                               95                                            Soybean   55 75     Sugar beet                                                                               20 0                                             Speedwell 60 --     Velvetleaf                                                                               40 0                                             sugar beet                                                                               90 65     Wheat     0  0                                             Umbrella sedge                                                                           -- 25     Wild buckwheat                                                                           40 30                                            Velvetleaf                                                                               100                                                                               100    Wild oat  0  20                                            Watergrass-2                                                                             -- 0                                                                 Wheat     40 15                                                                Wild buckwheat                                                                           95 100                                                               Wild oat  40 20                                                                Barnyardgrass-2                                                                          -- 10                                                                __________________________________________________________________________

TEST D

Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Convolvulus althaeoides), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia ), cocklebur (Xanthium pensylvanicum), common ragweed (Ambrosia artemisiifolia), tom (Zea mays), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnson grass (Sorghum halepense), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), signalgrass (Brachiaria platyphylla), smartweed (Polygonurn pensylvanicum), soybean (Glycine max), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), wooly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens), and purple nutsedge (Cyperus rotundus) tubers were planted into a matapeake sandy loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen em (one to four leaf stage), then treated postemergence with the test chemicals dissolved in a non-phytotoxic solvent. Pots receiving these postemergence treatments were placed in the greenhouse and maintained according to routine greenhouse procedures. Treated plants and untreated controls were maintained in the greenhouse approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table D, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control.

                  TABLE D                                                          ______________________________________                                         Rate 140 g/ha                                                                            Compound   Rate 70 g/ha Compound                                     Preemergence                                                                             9          Postemergence                                                                               9                                            ______________________________________                                         Barnyardgrass                                                                            95         Barnyardgrass                                                                               45                                           Bindweed  100        Bindweed     100                                          Blk nightshade                                                                           100        Blk nightshade                                                                              70                                           Cassia    20         Cassia       100                                          Cocklebur 55         Cocklebur    90                                           Corn      65         Corn         35                                           Cotton    20         Cotton       100                                          Crabgrass 100        Crabgrass    25                                           Fall panicum                                                                             95         Fall panicum 35                                           Giant foxtail                                                                            100        Giant foxtail                                                                               40                                           Green foxtail                                                                            100        Green foxtail                                                                               40                                           Jimsonweed                                                                               100        Jimsonweed   100                                          Johnson grass                                                                            90         Johnson grass                                                                               40                                           Morningglory                                                                             85         Morningglory 100                                          Nutsedge  40         Nutsedge     20                                           Pigweed   100        Pigweed      100                                          Prickly sida                                                                             100        Prickly sida 95                                           Ragweed   90         Ragweed      75                                           Shattercane                                                                              45         Shattercane  45                                           Signalgrass                                                                              100        Signalgrass  55                                           Smartweed 100        Smartweed    75                                           Soybean   20         Soybean      90                                           Sunflower 65         Sunflower    100                                          Velvetleaf                                                                               100        Velvetleaf   100                                          Wild proso                                                                               100        Wild proso   40                                           Yellow foxtail                                                                           100        Wooly cup grass                                                                             35                                                                Yellow foxtail                                                                              45                                           ______________________________________                                         Rate 70 g/ha                                                                             Compound  Rate 35 g/ha                                                                               Compound                                       Preemergence                                                                             9         Postemergence                                                                              4    8    9                                    ______________________________________                                         Barnyardgrass                                                                            75        Barnyardgrass                                                                              0    10   35                                   Bindweed  100       Bindweed    100  100  60                                   Blk nightshade                                                                           100       Blk nightshade                                                                             100  85   35                                   Cassia    0         Cassia      100  100  65                                   Cocklebur 45        Cocklebur   100  100  65                                   Corn      20        Corn        25   35   30                                   Cotton    0         Cotton      100  100  100                                  Crabgrass 85        Crabgrass   0    10   25                                   Fall panicum                                                                             95        Fall panicum                                                                               0    0    30                                   Giant foxtail                                                                            100       Giant foxtail                                                                              0    15   30                                   Green foxtail                                                                            100       Green foxtail                                                                              0    15   30                                   Jimsonweed                                                                               65        Jimsonweed  100  100  75                                   Johnson grass                                                                            60        Johnson grass                                                                              0    15   35                                   Morningglory                                                                             20        Morningglory                                                                               100  100  65                                   Nutsedge  20        Nutsedge    0    0    15                                   Pigweed   100       Pigweed     100  85   90                                   Prickly sida                                                                             100       Prickly sida                                                                               65   75   35                                   Ragweed   55        Ragweed     100  90   20                                   Shattercane                                                                              25        Shattercane 15   10   30                                   Signalgrass                                                                              85        Signalgrass 0    0    35                                   Smartweed 100       Smartweed   100  100  25                                   Soybean   0         Soybean     80   80   50                                   Sunflower 30        Sunflower   70   100  60                                   Velvetleaf                                                                               100       Velvetleaf  100  100  75                                   Wild proso                                                                               85        Wild proso  15   0    35                                   Yellow foxtail                                                                           95        Wooly cup grass                                                                            15   0    30                                                       Yellow foxtail                                                                             0    15   30                                   ______________________________________                                         Rate 35 g/ha                                                                             Compound  Rate 17 g/ha                                                                               Compound                                       Preemergence                                                                             9         Postemergence                                                                              4    8    9                                    ______________________________________                                         Barnyardgrass                                                                            55        Barnyardgrass                                                                              0    5    35                                   Bindweed  20        Bindweed    85   100  40                                   Blk nightshade                                                                           100       Blk nightshade                                                                             95   75   30                                   Cassia    0         Cassia      80   75   55                                   Cocklebur 30        Cocklebur   85   100  60                                   Corn      0         Corn        20   30   25                                   Cotton    0         Cotton      100  100  100                                  Crabgrass 55        crabgrass   0    5    15                                   Fall panicum                                                                             95        Fall panicum                                                                               0    0    25                                   Giant foxtail                                                                            50        Giant foxtail                                                                              0    15   25                                   Green foxtail                                                                            50        Green foxtail                                                                              0    15   25                                   Jimsonweed                                                                               10        Jimsonweed  100  95   70                                   Johnson grass                                                                            15        Johnson grass                                                                              0    10   30                                   Morningglory                                                                             0         Morningglory                                                                               100  100  40                                   Nutsedge  0         Nutsedge    0    0    15                                   Pigweed   100       Pigweed     90   75   90                                   Prickly sida                                                                             100       Prickly sida                                                                               55   65   25                                   Ragweed   45        Ragweed     100  75   15                                   Shattercane                                                                              15        Shattercane 10   5    25                                   Signalgrass                                                                              0         Signalgrass 0    0    30                                   Smartweed 100       Smartweed   100  90   25                                   Soybean   0         Soybean     70   75   35                                   Sunflower 0         Sunflower   65   85   55                                   Velvetleaf                                                                               65        Velvetleaf  100  100  55                                   Wild proso                                                                               25        Wild proso  10   0    30                                   Yellow foxtail                                                                           40        Wooly cup grass                                                                            10   0    25                                                       Yellow foxtail                                                                             0    10   25                                   ______________________________________                                         Rate 17 g/ha                                                                             Compound  Rate 8 g/ha Compound                                       Preemergence                                                                             9         Postemergence                                                                              4    8    9                                    ______________________________________                                         Barnyardgrass                                                                            15        Barnyardgrass                                                                              0    0    30                                   Bindweed  0         Bindweed    70   80   35                                   Blk nightshade                                                                           100       Blk nightshade                                                                             60   70   25                                   Cassia    0         Cassia      60   65   50                                   Cocklebur 15        Cocklebur   55   80   20                                   Corn      0         Corn        20   20   25                                   Cotton    0         Cotton      100  100  100                                  Crabgrass 15        Crabgrass   0    0    10                                   Fall panicum                                                                             35        Fall panicum                                                                               0    0    20                                   Giant foxtail                                                                            10        Giant foxtail                                                                              0    10   25                                   Green foxtail                                                                            10        Green foxtail                                                                              0    10   20                                   Jimsonweed                                                                               0         Jimsonweed  100  80   65                                   Johnson grass                                                                            0         Johnson grass                                                                              0    0    25                                   Morningglory                                                                             0         Morningglory                                                                               100  65   35                                   Nutsedge  0         Nutsedge    0    0    0                                    Pigweed   100       Pigweed     65   70   85                                   Prickly sida                                                                             65        Prickly sida                                                                               45   45   20                                   Ragweed   15        Ragweed     65   65   10                                   Shattercane                                                                              10        Shattercane 0    0    20                                   Signalgrass                                                                              0         Signalgrass 0    0    25                                   Smartweed 100       Smartweed   55   80   20                                   Soybean   0         Soybean     65   70   20                                   Sunflower 0         Sunflower   60   55   50                                   Velvetleaf                                                                               40        Velvetleaf  100  65   45                                   Wild proso                                                                               15        Wild proso  0    0    25                                   Yellow foxtail                                                                           10        Wooly cup grass                                                                            5    0    20                                                       Yellow foxtail                                                                             0    5    20                                   ______________________________________                                         Rate 8 g/ha                                                                              Compound  Rate 4 g/ha Compound                                       Preemergence                                                                             9         Postemergence                                                                              4    8    9                                    ______________________________________                                         Barnyardgrass                                                                            0         Barnyardgrass                                                                              0    0    15                                   Bindweed  0         Bindweed    25   65   15                                   Blk nightshade                                                                           100       Blk nightshade                                                                             40   60   20                                   Cassia    0         Cassia      20   35   10                                   Cocklebur 0         Cocklebur   45   65   15                                   Corn      0         Corn        15   15   20                                   Cotton    0         Cotton      75   100  100                                  Crabgrass 0         Crabgrass   0    0    0                                    Fall panicum                                                                             0         Fall panicum                                                                               0    0    10                                   Giant foxtail                                                                            0         Giant foxtail                                                                              0    0    10                                   Green foxtail                                                                            0         Green foxtail                                                                              0    0    10                                   Jimsonweed                                                                               0         Jimsonweed  100  65   10                                   Johnson grass                                                                            0         Johnson grass                                                                              0    0    15                                   Morningglory                                                                             0         Morningglory                                                                               95   60   10                                   Nutsedge  0         Nutsedge    0    0    0                                    Pigweed   90        Pigweed     55   55   10                                   Prickly sida                                                                             20        Prickly sida                                                                               25   15   0                                    Ragweed   0         Ragweed     35   40   0                                    Shattercane                                                                              0         Shattercane 0    0    10                                   Signalgrass                                                                              0         Signalgrass 0    0    15                                   Smartweed 55        Smartweed   0    60   15                                   Soybean   0         Soybean     40   60   15                                   Sunflower 0         Sunflower   55   45   40                                   Velvetleaf                                                                               15        Velvetleaf  55   45   15                                   Wild proso                                                                               0         Wild proso  0    0    20                                   Yellow foxtail                                                                           0         Wooly cup grass                                                                            0    0    15                                                       Yellow foxtail                                                                             0    0    10                                   ______________________________________                                         Rate 2 g/ha     Compound                                                       Postemergence   4           8                                                  ______________________________________                                         Barnyardgrass   0           0                                                  Bindweed        0           45                                                 Blk nightshade  0           40                                                 Cassia          10          10                                                 Cocklebur       30          50                                                 Corn            10          10                                                 Cotton          --          100                                                Crabgrass       0           0                                                  Fall panicum    0           0                                                  Giant foxtail   0           0                                                  Green foxtail   0           0                                                  Jimsonweed      100         55                                                 Johnson grass   0           0                                                  Morningglory    35          40                                                 Nutsedge        0           0                                                  Pigweed         45          35                                                 Prickly sida    0           0                                                  Ragweed         30          25                                                 Shattercane     0           0                                                  Signalgrass     0           0                                                  Smartweed       0           35                                                 Soybean         10          15                                                 Sunflower       35          20                                                 Velvetleaf      45          20                                                 Wild proso      0           0                                                  Wooly cup grass 0           0                                                  Yellow foxtail  0           0                                                  ______________________________________                                     

We claim:
 1. A compound of the formula ##STR51## wherein: X is selected from the group O, S, S(O), S(O)₂, CHOCH₂ F, CHOCHF₂, CHOCF₃, CHOCH₂ CF₃ and NR⁴ ;m and n are independently 1 or 2, where m+n=2 or 3; p is 0 to 9; U is N or CH; W is independently O or S; R^(A) is independently selected from the group halogen, C₁ -C₄ alkyl, cyano, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₂ -C₄ alkylcarbonyl, OR³, C₂ -C₆ alkyloxycarbonyl, C₂ -C₆ haloalkoxycarbonyl, and C₃ -C₈ alkoxycarbonylalkyl; or, two R^(A) groups on the same carbon atom, together with this carbon, are C═O; R³ is selected from the group hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkylcarbonyl and C₂ -C₄ haloalkylcarbonyl; R⁴ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₂ -C₄ alkylcarbonyl, C₂ -C₄ haloalkoxycarbonyl and C₂ -C₄ alkoxycarbonyl; provided that when X is CHOCH₂ F, CHOCHF₂, CHOCF₃, or CHOCH₂ CF₃, m and n are 1, and U is N, then p is 1 to 5 and at least one R^(A) is other than alkyl; Q is selected from the group ##STR52## Z is O or S; R⁵ is hydrogen or halogen; R⁶ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, OCH₃, SCH₃, OCHF₂, halogen, CN and NO₂ ; R⁷ is selected from the group hydrogen, C₁ -C₈ alkyl, C₁ -C₈ haloalkyl, halogen, OR¹¹, SR¹¹, S(O)_(q) R¹¹, COR¹¹, CO₂ R¹¹, C(O)SR¹¹, C(O)NR¹² R¹³, CHO and NHSO₂ NHR¹⁶ ; R⁸ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and halogen; R⁹ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and halogen; or, when Q is Q-2 or Q-6, R⁸ and R⁹ together with the carbon to which they are bonded is additionally selected from C═O; R¹⁰ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkoxyalkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkynyl; R¹¹ is selected from the group C₁ -C₈ alkyl, C₃ -C₈ cycloalkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, C₂ -C₈ alkylsulphinylalkyl, C₂ -C₈ alkylsulphonylalkyl, C₃ -C₈ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl, C₂ -C₄ carboxyalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₆ -C₈ alkenyloxycarbonylalkyl, C₆ -C₈ alkynyloxycarbonylalkyl, C₅ -C₈ alkoxycarbonylalkenyl, C₄ -C₈ alkenyloxyalkyl, C₆ -C₈ cycloalkoxyalkyl, C₄ -C₈ alkynyloxyalkyl, C₃ -C₈ haloalkoxyalkyl, C₄ -C₈ haloalkenyloxyalkyl, C₄ -C₈ haloalkynyloxyalkyl, C₄ -C₈ alkenylthioalkyl, C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted with phenoxy or benzyloxy, each of the phenoxy and benzyloxy optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl, C₄ -C₈ trialkylsilylalkyl, C₃ -C₈ cyanoalkyl, C₃ -C₈ halocycloalkyl, C₃ -C₈ haloalkenyl, C₅ -C₈ alkoxyalkenyl, C₅ -C₈ haloalkoxyalkenyl, C₅ -C₈ alkylthioalkenyl, C₃ -C₈ haloalkynyl, C₅ -C₈ alkoxyalkynyl, C₅ -C₈ haloalkoxyalkynyl, C₅ -C₈ alkylthioalkynyl, C₂ -C₈ alkylcarbonyl; benzyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁷ COR¹⁸, CHR⁷ P(O)(ORI¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S)(OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O)NH₂, phenyl and pyridyl, each of the phenyl and pyridyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy and CHR¹⁷ CH═NOR¹⁸ ; R¹² and R¹⁴ are independently hydrogen or C₁ -C₄ alkyl; R¹³ and R¹⁵ are independently selected from the group C₁ -C₄ alkyl and phenyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and C₁ -C₄ alkoxy; or R¹² and R¹³ are taken together as --(CH₂)₅ --, --(CH₂)₄ -- or --CH₂ CH₂ OCH₂ CH₂ --, each independently forming a ring in which one or more H atoms is optionally replaced by at least one member independently selected from the group C₁ -C₃ alkyl, optionally substituted phenyl and optionally substituted benzyl; or R¹⁴ and R¹⁵ together with the carbon atom to which they are attached is C₃ -C₈ cycloalkyl; R¹⁶ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl; R¹⁷ is hydrogen or C₁ -C₃ alkyl; R¹⁸ is selected from the group C₁ -C₆ alkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkynyl; and q is 1 or2.
 2. A compound according to claim 1, wherein:X is group O; R^(A) is independently selected from the group fluorine, chlorine and bromine; R⁵ is selected from the group hydrogen, fluorine and chlorine; R⁶ is selected from the group chlorine, bromine and cyano; R⁷ is selected from the group hydrogen, OR¹¹, CO₂ R¹¹, C₁ -C₂ alkyl and C₁ -C₂ haloalkyl; R¹⁰ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, C₃ -C₄ alkenyl and C₃ -C₄ alkynyl; R¹¹ is selected from the group C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkylthioalkyl, C₂ -C₄ alkylsulphinylalkyl, C₂ -C₄ alkylsulphonylalkyl, C₃ -C₆ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl, C₂ -C₄ carboxyalkyl, C₃ -C₆ alkoxycarbonylalkyl, C₆ -C₈ alkenyloxycarbonylalkyl, C₆ -C₈ alkynyloxycarbonylalkyl, C₅ -C₆ alkoxycarbonylalkenyl, C₆ -C₈ cycloalkoxyalkyl, C₄ -C₆ alkenyloxyalkyl, C₄ -C₆ alkynyloxyalkyl, C₃ -C₆ haloalkoxyalkyl, C₄ -C₈ haloalkenoxyalkyl, C₄ -C₆ haloalkynyloxyalkyl, C₆ -C₈ cycloalkylthioalkyl, C₄ -C₆ alkenylthioalkyl, C₄ -C₆ alkynylthioalkyl; C₁ -C₂ alkyl substituted with phenoxy or benzyloxy, each of the phenoxy and benzyloxy optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; C₄ -C₈ trialkylsilylalkyl, C₃ -C₄ cyanoalkyl, C₃ -C₆ halocycloalkyl, C₃ -C₆ haloalkenyl, C₅ -C₆ alkoxyalkenyl, C₅ -C₆ haloalkoxyalkenyl, C₅ -C₆ alkylthioalkenyl, C₃ -C₆ haloalkynyl, C₅ -C₆ alkoxyalkynyl, C₅ -C₆ haloalkoxyalkynyl, C₅ -C₆ alkylthioalkynyl, C₂ -C₄ alkylcarbonyl, benzyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₂ alkyl and C₁ -C₂ haloalkyl; CHR¹⁷ COR¹⁸, CHR¹⁷ P(O)(OR¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S)(OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O)NH₂, phenyl and pyridyl, each of the phenyl and pyridyl optionally substituted with at least one member independently selected from the group fluorine, chlorine, bromine, C₁ -C₂ alkylhaloalkyl and C₁ 1∝C₂ alkoxy; R¹² is hydrogen or C₁ -C₂ alkyl; R¹³ is selected from the group C₁ -C₂ alkyl and phenyl optionally substituted with at least one member selected from the group fluorine, chlorine, bromine, C₁ -C₂ alkyl, C₁ -C₂ haloalkyl and C₁ -C₂ alkoxy; or R¹² and R¹³ are taken together as --(CH₂)₅ --, --(CH₂)₄ -- or --CH₂ CH₂ OCH₂ CH₂ --, each independently forming a ring in which one or more H atoms is optionally and independently replaced by C₁ -C₂ alkyl; R¹⁷ is hydrogen or C₁ -C₂ alkyl; and R¹⁸ is selected from the group C₁ -C₂ alkyl, C₃ -C₄ alkenyl and C₃ -C₄ alkynyl.
 3. A process for making a compound of Formula I ##STR53## wherein: X is selected from the group O, S, S(O), S(O)₂, CH₂, CHF, CF₂, CHCl, CHBr, CHOCH₂ F, CHOCHF₂, CHOCF₃, CHOCH₂ CF₃ and NR⁴ ;m and n are independently 1 or 2, where m+n=2 or 3; p is 0 to 9; U is N or CH; W is independently O or S; R^(A) is independently selected from the group halogen, C₁ -C₄ alkyl, cyano, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₂ -C₄ alkylcarbonyl, OR³, C₂ -C₆ alkyloxycarbonyl, C₂ -C₆ haloalkoxycarbonyl, and C₃ -C₈ alkoxycarbonylalkyl; or, two R^(A) groups on the same carbon atom, together with this carbon, are C═O; R³ is selected from the group hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkylcarbonyl and C₂ -C₄ haloalkylcarbonyl; R⁴ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₂ -C₄ alkylcarbonyl, C₂ -C₄ haloalkoxycarbonyl and C₂ -C₄ alkoxycarbonyl; Q is selected from the group ##STR54## Z is O or S; R⁵ is hydrogen or halogen; R⁶ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, OCH₃, SCH₃, OCHF₂, halogen, CN and NO₂ ; R⁷ is selected from the group hydrogen, C₁ -C₈ alkyl, C₁ -C₈ haloalkyl, halogen, OR¹¹, SR¹¹, S(O)_(q) R¹¹, COR¹¹, CO₂ R¹¹, C(O)SR¹¹, C(O)NR¹² R¹³, CHO and NHSO₂ NHR¹⁶ ; R⁸ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and halogen; R⁹ is selected from the group hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and halogen; or, when Q is Q-2 or Q-6, R⁸ and R⁹ together with the carbon to which they are bonded is additionally selected from C═O; R¹⁰ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkoxyalkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkynyl; R¹¹ is selected from the group C₁ -C₈ alkyl, C₃ -C₈ cycloalkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, C₂ -C₈ alkylsulphinylalkyl, C₂ -C₈ alkylsulphonylalkyl, C₃ -C₈ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl, C₂ -C₄ carboxyalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₆ -C₈ alkenyloxycarbonylalkyl, C₆ -C₈ alkynyloxycarbonylalkyl, C₅ -C₈ alkoxycarbonylalkenyl, C₄ -C₈ alkenyloxyalkyl, C₆ -C₈ cycloalkoxyalkyl, C₄ -C₈ alkynyloxyalkyl, C₃ -C₈ haloalkoxyalkyl, C₄ -C₈ haloalkenyloxyalkyl, C₄ -C₈ haloalkynyloxyalkyl, C₄ -C₈ alkenylthioalkyl, C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted with phenoxy or benzyloxy, each of the phenoxy and benzyloxy optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl, C₄ -C₈ trialkylsilylalkyl, C₃ -C₈ cyanoalkyl, C₃ -C₈ halocycloalkyl, C₃ -C₈ haloalkenyl, C₅ -C₈ alkoxyalkenyl, C₅ -C₈ haloalkoxyalkenyl, C₅ -C₈ alkylthioalkenyl, C₃ -C₈ haloalkynyl, C₅ -C₈ alkoxyalkynyl, C₅ -C₈ haloalkoxyalkynyl, C₅ -C₈ alkylthioalkynyl, C₂ -C₈ alkylcarbonyl; benzyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁷ COR¹⁸, CHR⁷ P(O)(ORI¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S)(OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O)NH₂, phenyl and pyridyl, each of the phenyl and pyridyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy and CHR¹⁷ CH═NOR¹⁸ ; R¹² and R¹⁴ are independently hydrogen or C₁ -C₄ alkyl; R¹³ and R¹⁵ are independently selected from the group C₁ -C₄ alkyl and phenyl optionally substituted with at least one member independently selected from the group halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl and C₁ -C₄ alkoxy; or R¹² and R¹³ are taken together as --(CH₂)₅ --, --(CH₂)₄ -- or --CH₂ CH₂ OCH₂ CH₂ --, each independently forming a ring in which one or more H atoms is optionally replaced by at least one member independently selected from the group C₁ -C₃ alkyl, optionally substituted phenyl and optionally substituted benzyl; or R¹⁴ and R¹⁵ together with the carbon atom to which they are attached is C₃ -C₈ cycloalkyl; R¹⁶ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl; R¹⁷ is hydrogen or C₁ -C₃ alkyl; R¹⁸ is selected from the group C₁ -C₆ alkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkynyl; and q is 1 or 2comprising one of the following steps: a) reacting a compound of Formula II with a compound of Formula III, ##STR55## wherein R=hydroxy, C₁ -C₄ alkoxy, halogen or O-active ester, optionally in the presence of a solvent; b) reacting a compound of Formula IV, ##STR56## wherein Y is selected from the group O, S and NH, with a compound of Formula V, VI or VII, ##STR57## wherein Z is selected from the group chlorine, bromine, iodine, O--SO₂ CH₃, O--SO₂ CF₃, O--SO₂ --Ph, and ##STR58## c) reacting a compound of Formula HI first with a compound of Formula XV, wherein L¹ and L² are independently selected leaving groups, to form a compound of Formula VIII, then, with a compound of Formula IX to form a compound of Formula X, ##STR59## and cyclizing the compound of Formula X; and d) reacting a compound of Formula XI with a compound of Formula XVb optionally in the presence of a diluent and optionally in the presence of an acid-acceptor, ##STR60## wherein R¹ is independently H or R^(A;) and R¹⁹ is independently selected from the group H, C_(1-C) ₄ alkyl, C₁ -C₄ haloalkyl, and C₃ -C₄ alkenyl.
 4. A herbicidal composition comprising an herbicidally effective mount of a compound according to claim 1 and a carrier therefor.
 5. A method of controlling unwanted vegetation comprising applying to the unwanted vegetation or the environment in which it is grown an herbicidally effective amount of a compound according to claim
 1. 